CN106083673A - A kind of preparation technology of carbocisteine - Google Patents
A kind of preparation technology of carbocisteine Download PDFInfo
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- CN106083673A CN106083673A CN201610488728.2A CN201610488728A CN106083673A CN 106083673 A CN106083673 A CN 106083673A CN 201610488728 A CN201610488728 A CN 201610488728A CN 106083673 A CN106083673 A CN 106083673A
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- carbocisteine
- preparation technology
- cysteine hydrochloride
- monoxone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the preparation technology of a kind of compound, the preparation technology of a kind of carbocisteine, belong to technical field of organic synthesis；The preparation technology of described carbocisteine, comprise the following steps: (a) takes L cysteine hydrochloride monohydrate and solid monoxone, wherein monoxone is with 60 70% taken amounts of L cysteine hydrochloride monohydrate quality, b L cysteine hydrochloride monohydrate and monoxone are added water stirring and dissolving by (), it is 15 25 DEG C that course of dissolution controls system temperature, the PH of (c) regulation system to 7.0 7.5, the temperature of control system is 45 50 DEG C, stir and react, d () reacts complete, the PH of regulation system to 6.0 6.4, decolour, adsorbing contaminant processes, e () filters, the PH to 2.8 3.0 of regulation filtrate, cooling obtains carbocisteine crystallization；The carbocisteine that this process route prepares, has purity height, yield height, the advantage of good stability, and process route is succinct, it is easy to operate and control.
Description
Technical field
The present invention relates to the preparation technology of a kind of compound, the preparation technology of a kind of carbocisteine, belong to organic
Synthesis technical field.
Background technology
Carbocisteine is a kind of medicine, is mainly used in the sputum that the disease such as chronic bronchitis, bronchial asthma causes and glues
The treatment that thick, dys-expectoration and stagnation of phlegm plug trachea etc. are sick.Carbocisteine is also a kind of important medicine intermediate and chemical industry simultaneously
Raw material.
Carbocisteine has multiple synthetic route and synthetic method, and one of which synthetic route is to use Cys salt
Hydrochlorate one water thing and monoxone are that raw material synthesizes.CN103102294A discloses one and utilizes L-cysteine hydrochloride
One water thing and liquid chlorine acetic acid carry out the synthetic method of carbocisteine, but under these process conditions, the yield of carbocisteine is relatively low, pure
Spending the most not ideal enough, it is the biggest that pilot process controls difficulty.
Summary of the invention
The goal of the invention of the present invention is: for the problem of above-mentioned existence, it is provided that a kind of with L-cysteine hydrochloride one
Water thing and monoxone are raw material, carry out technique prepared by carbocisteine, improve preparation efficiency and the quality of carbocisteine.
The technical solution used in the present invention is as follows:
A kind of preparation technology of carbocisteine, it is characterised in that: comprise the following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein monoxone is with L-cysteine hydrochloride one water
The 60-70% taken amount of material amount；
B L-cysteine hydrochloride one water thing and monoxone are added water stirring and dissolving by (), it is 15-that course of dissolution controls system temperature
25℃；
C the PH to 7.0-7.5 of () regulation system, the temperature controlling system is 45-50 DEG C, stirs and react；
D () reacts complete, the PH to 6.0-6.4 of regulation system, carries out decolouring, adsorbing contaminant processes；
E () filters, the PH to 2.8-3.0 of regulation filtrate, and cooling obtains carbocisteine crystallization.
The preparation technology of the carbocisteine of the present invention uses L-cysteine hydrochloride one water thing and solid monoxone to be former
Material, the monoxone effective content in solid monoxone is high, it is possible to be greatly improved preparation efficiency and quality, simultaneously at L-half Guang ammonia
In acid hydrochloride one water thing and the chloroacetic dissolution system of solid, by the control of temperature, the reaction end can be effectively improved in solution
The concentration of thing, it is ensured that the efficiency of production and productivity.It addition, this technique passes through pH value and the temperature design of reaction system, reach to protect
Card reaction efficiency and the purpose of quality.
Further, in described step (b), water is with the 300-400% taken amount of L-cysteine hydrochloride one water substance amount.
The water of this quality makes the concentration of system be in applicable scope so that controls difficulty in system each operation later and is dropped
Low, and the optimization of beneficially reaction yield.
Further, in described step (c), while regulation system PH, it is additionally added ammonium hydrogen carbonate.Ammonium hydrogen carbonate is in reaction
During, serve taking out of in time of the effect of efficient regulation system temperature, beneficially system heat, prevent the solution of local
The decomposition of the L-cysteine hydrochloride one water thing that temperature is too high and causes, it is ensured that the economy of process.
Further, described ammonium hydrogen carbonate is with the 120-140% taken amount of L-cysteine hydrochloride one water substance amount.To protect
Heat is the most sufficiently taken out of system by card.
Further, in described step (c), with the PH of liquefied ammonia regulation system.Liquefied ammonia also has certain thermoregulatory effect, it is ensured that
The temperature of system is in opereating specification, and additionally in time, efficiency is high in the neutralization reaction of liquefied ammonia.
Further, in described step (c), the PH of regulation system to 7.5.Under this PH, reaction has reversal rate height, controlled
The advantage that property is good, and productivity and purity preferable.
Further, in described step (c), the response time is 30-120 minute.System is sufficiently reacted, protects
Card yield.
Further, in described step (d), use activated carbon to carry out decolouring, adsorbing contaminant processes.
Further, in described step (d), decolouring, the temperature of adsorbing contaminant processing controls system are 75-80 DEG C.
Further, in described step (d), decolouring, adsorbing contaminant process time are 30-120 minute.
At the process conditions, be conducive to reaching preferably decolouring, adsorbing contaminant treatment effect.
Further, in described step (e), the PH process of regulation filtrate is time-consumingly not more than 30 minutes.Pass through regulating time
Control the speed of height such as control, the chlorinity in crystalline product can be effectively reduced, improve the quality of product.
Further, in described step (e), with the PH of hydrochloric acid regulation filtrate.
Further, also include, by step (e) gained crystallization dissolving with hydrochloric acid, regulating the PH to 0.5-1.0 of this solution, entering
Row decolouring, adsorbing contaminant process, and filter, and regulate the PH to 2.8-3.0 of filtrate, and cooling obtains carbocisteine crystallization again.Logical
Cross refinement treatment again so that the product purity of preparation is higher, simultaneously by the control of technique, it is possible to ensure returning of carbocisteine
Receive.
Further, during the most dissolving crystallized, the temperature that decolouring, adsorbing contaminant process is 75-80 DEG C, decolouring,
The adsorbing contaminant process time is 30-120 minute, and the time-consuming of PH to 2.8-3.0 process again regulating filtrate is not more than 30 minutes.
In sum, owing to have employed technique scheme, the invention has the beneficial effects as follows: the carboxylic that this process route prepares
First department is smooth, has purity height, yield height, the advantage of good stability, and process route is succinct, it is easy to operate and control.
Detailed description of the invention
All features disclosed in this specification, or disclosed all methods or during step, except mutually exclusive
Feature and/or step beyond, all can combine by any way.
Any feature disclosed in this specification, unless specifically stated otherwise, all can by other equivalence or there is similar purpose
Alternative features is replaced.I.e., unless specifically stated otherwise, an example during each feature is a series of equivalence or similar characteristics
?.
In following embodiment, L-cysteine hydrochloride one water thing and solid monoxone all use commercial goods.
Embodiment 1
The preparation technology of the carbocisteine of the present embodiment, is realized by following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein, L-cysteine hydrochloride one water thing is
150KG, monoxone is with 60% taken amount of L-cysteine hydrochloride one water substance amount, i.e. 90KG；
B reactant L-cysteine hydrochloride one water thing and monoxone are put in reactor by (), add water 600KG stirring and dissolving,
It is about 20 DEG C that course of dissolution carries out heating to control system temperature；
C (), with liquefied ammonia, is simultaneously introduced ammonium hydrogen carbonate, with the PH to 7.5 of regulation system, the addition of ammonium hydrogen carbonate is 200KG, with
Time control system temperature be 45-50 DEG C, stirring react 30 minutes；
D () reacts complete, with the PH to 6.0 of hydrochloric acid regulation system, and add 20kg activated carbon and carry out decolouring, at adsorbing contaminant
Reason, in decolouring, adsorbing contaminant processing procedure, the temperature of system is 75 DEG C, and the process time is 30 minutes；
E () filters, with the PH to 2.8 of hydrochloric acid regulation filtrate, whole regulation process control was at about 20 minutes, and cooling obtains carboxylic first
Take charge of smooth crystallization.
After testing, gained crystallization is carbocisteine, and its purity is 99.2%, in terms of L-cysteine hydrochloride one water thing, and carboxylic
The smooth yield of first department is 96%.
Embodiment 2
The preparation technology of the carbocisteine of the present embodiment, is realized by following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein, L-cysteine hydrochloride one water thing is
150KG, monoxone is with 60% taken amount of L-cysteine hydrochloride one water substance amount, i.e. 90KG；
B reactant L-cysteine hydrochloride one water thing and monoxone are put in reactor by (), add water 600KG stirring and dissolving,
It is about 20 DEG C that course of dissolution carries out heating to control system temperature；
C () is 45-50 DEG C by the PH to 7.5 of liquefied ammonia regulation system, the temperature controlling system, react 30 minutes at stirring；
D () reacts complete, with the PH to 6.0 of hydrochloric acid regulation system, and add 20kg activated carbon and carry out decolouring, at adsorbing contaminant
Reason, in decolouring, adsorbing contaminant processing procedure, the temperature of system is 75 DEG C, and the process time is 30 minutes；
E () filters, with the PH to 2.8 of hydrochloric acid regulation filtrate, whole regulation process control was at about 20 minutes, and cooling obtains carboxylic first
Take charge of smooth crystallization.
After testing, gained crystallization is carbocisteine, and its purity is 98.9%, in terms of L-cysteine hydrochloride one water thing, and carboxylic
The smooth yield of first department is 90%.
Embodiment 3
The preparation technology of the carbocisteine of the present embodiment, is realized by following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein, L-cysteine hydrochloride one water thing is
150KG, monoxone is with 70% taken amount of L-cysteine hydrochloride one water substance amount, i.e. 105KG；
B reactant L-cysteine hydrochloride one water thing and monoxone are put in reactor by (), add water 450KG stirring and dissolving,
It is about 25 DEG C that course of dissolution carries out heating to control system temperature；
C (), with liquefied ammonia, is simultaneously introduced ammonium hydrogen carbonate, with the PH to 7.5 of regulation system, the addition of ammonium hydrogen carbonate is 210KG, with
Time control system temperature be 45-50 DEG C, stirring react 90 minutes；
D () reacts complete, with the PH to 6.4 of hydrochloric acid regulation system, and add 20kg activated carbon and carry out decolouring, at adsorbing contaminant
Reason, in decolouring, adsorbing contaminant processing procedure, the temperature of system is 80 DEG C, and the process time is 90 minutes；
E () filters, with the PH to 3.0 of hydrochloric acid regulation filtrate, whole regulation process control was at about 30 minutes, and cooling obtains carboxylic first
Take charge of smooth crystallization.
After testing, gained crystallization is carbocisteine, and its purity is 98.9%, in terms of L-cysteine hydrochloride one water thing, and carboxylic
The smooth yield of first department is 94%.
Embodiment 4
The preparation technology of the carbocisteine of the present embodiment, is realized by following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein, L-cysteine hydrochloride one water thing is
150KG, monoxone is with 70% taken amount of L-cysteine hydrochloride one water substance amount, i.e. 105KG；
B reactant L-cysteine hydrochloride one water thing and monoxone are put in reactor by (), add water 450KG stirring and dissolving,
It is about 25 DEG C that course of dissolution carries out heating to control system temperature；
C (), with liquefied ammonia, is simultaneously introduced ammonium hydrogen carbonate, with the PH to 7.5 of regulation system, the addition of ammonium hydrogen carbonate is 210KG, with
Time control system temperature be 45-50 DEG C, stirring react 90 minutes；
D () reacts complete, with the PH to 6.4 of hydrochloric acid regulation system, and add 20kg activated carbon and carry out decolouring, at adsorbing contaminant
Reason, in decolouring, adsorbing contaminant processing procedure, the temperature of system is 80 DEG C, and the process time is 90 minutes；
E () filters, with the PH to 3.0 of hydrochloric acid regulation filtrate, whole regulation process control was at about 50 minutes, and cooling obtains carboxylic first
Take charge of smooth crystallization.
After testing, gained crystallization is carbocisteine, and its purity is 98.8%, in terms of L-cysteine hydrochloride one water thing, and carboxylic
The smooth yield of first department is 95%, the chlorinity 0.15% of product, and embodiment 3 products obtained therefrom chlorinity is 0.03%, it is seen that step (e)
The long increase causing chlorinity of regulating time.
Embodiment 5
The preparation technology of the carbocisteine of the present embodiment, is realized by following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein, L-cysteine hydrochloride one water thing is
150KG, monoxone is with 65% taken amount of L-cysteine hydrochloride one water substance amount, i.e. 97.5KG；
B reactant L-cysteine hydrochloride one water thing and monoxone are put in reactor by (), add water 525KG stirring and dissolving,
It is about 15 DEG C that course of dissolution carries out heating to control system temperature；
C (), with liquefied ammonia, is simultaneously introduced ammonium hydrogen carbonate, with the PH to 7.0 of regulation system, the addition of ammonium hydrogen carbonate is 180KG, with
Time control system temperature be 45-50 DEG C, stirring react 120 minutes；
D () reacts complete, with the PH to 6.2 of hydrochloric acid regulation system, and add 20kg activated carbon and carry out decolouring, at adsorbing contaminant
Reason, in decolouring, adsorbing contaminant processing procedure, the temperature of system is 78 DEG C, and the process time is 120 minutes；
E () filters, with the PH to 3.0 of hydrochloric acid regulation filtrate, whole regulation process control was at about 20 minutes, and cooling obtains carboxylic first
Take charge of smooth crystallization.
After testing, gained crystallization is carbocisteine, and its purity is 99.0%, in terms of L-cysteine hydrochloride one water thing, and carboxylic
The smooth yield of first department is 95.5%.
Embodiment 6
The preparation technology of the carbocisteine of the present embodiment, is realized by following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein, L-cysteine hydrochloride one water thing is
150KG, monoxone is with 65% taken amount of L-cysteine hydrochloride one water substance amount, i.e. 97.5KG；
B reactant L-cysteine hydrochloride one water thing and monoxone are put in reactor by (), add water 600KG stirring and dissolving,
It is about 15 DEG C that course of dissolution carries out heating to control system temperature；
C () uses the PH to 7.3 of sodium hydroxide regulation system, the addition of ammonium hydrogen carbonate is 180KG simultaneously, controls system simultaneously
Temperature is 45-50 DEG C, reacts 120 minutes at stirring；
D () reacts complete, with the PH to 6.2 of hydrochloric acid regulation system, and add 20kg activated carbon and carry out decolouring, at adsorbing contaminant
Reason, in decolouring, adsorbing contaminant processing procedure, the temperature of system is 78 DEG C, and the process time is 120 minutes；
E () filters, with the PH to 2.8 of hydrochloric acid regulation filtrate, whole regulation process control was at about 20 minutes, and cooling obtains carboxylic first
Take charge of smooth crystallization.
After testing, gained crystallization is carbocisteine, and its purity is 99.1%, in terms of L-cysteine hydrochloride one water thing, and carboxylic
The smooth yield of first department is 93.5%.
Embodiment 7
Carbocisteine obtained by embodiment 1 to 6 is crystallized, respectively with dissolving with hydrochloric acid, and regulates the PH to 0.5 of this solution, adopt
With activated carbon carry out decolouring, adsorbing contaminant processes, the temperature that decolouring, adsorbing contaminant process is 75 DEG C, decolouring, adsorbing contaminant time
Being 120 minutes, filter, and regulate the PH to 2.8 of filtrate, time-consuming about 30 minutes of this regulation process, cooling obtains carboxylic first department again
Smooth crystallization.
After testing, gained crystallization is carbocisteine, and its purity is up to 99.6%.
Embodiment 8
By the carbocisteine obtained by embodiment 1 to 6, crystallization dissolving with hydrochloric acid, and regulate the PH to 1.0 of this solution, use and live
Property charcoal carries out decolouring, adsorbing contaminant processes, the temperature that decolouring, adsorbing contaminant process is 80 DEG C, and decolouring, adsorbing contaminant time are 30
Minute, filtering, and regulate the PH to 3.0 of filtrate, time-consuming about 20 minutes of this regulation process, cooling obtains carbocisteine knot again
Brilliant.
After testing, gained crystallization is carbocisteine, and its purity is up to 99.7%.
Meanwhile, inventor is according to carbocisteine obtained by CN103102294A process route, and its purity about 95%, with L-half
Cystine hydrochloride one water thing meter, carbocisteine yield about 85%, it is seen that the carbocisteine that this process route prepares, there is purity
High, yield height, the advantage of good stability, and process route is succinct, it is easy to operate and control.
The invention is not limited in aforesaid detailed description of the invention.The present invention expands to any disclose in this manual
New feature or any new combination, and the arbitrary new method that discloses or the step of process or any new combination.
Claims (10)
1. the preparation technology of a carbocisteine, it is characterised in that: comprise the following steps:
A () takes L-cysteine hydrochloride one water thing and solid monoxone, wherein monoxone is with L-cysteine hydrochloride one water
The 60-70% taken amount of material amount；
B L-cysteine hydrochloride one water thing and monoxone are added water stirring and dissolving by (), it is 15-that course of dissolution controls system temperature
25℃；
C the PH to 7.0-7.5 of () regulation system, the temperature controlling system is 45-50 DEG C, stirs and react；
D () reacts complete, the PH to 6.0-6.4 of regulation system, carries out decolouring, adsorbing contaminant processes；
E () filters, the PH to 2.8-3.0 of regulation filtrate, and cooling obtains carbocisteine crystallization.
2. the preparation technology of carbocisteine as claimed in claim 1, it is characterised in that: in described step (c), regulation system PH
While be additionally added ammonium hydrogen carbonate.
3. the preparation technology of carbocisteine as claimed in claim 2, it is characterised in that: described ammonium hydrogen carbonate is with Cys
The 120-140% taken amount of hydrochloride monohydrate quality.
4. the preparation technology of carbocisteine as claimed in claim 1, it is characterised in that: in described step (c), regulate with liquefied ammonia
The PH of system.
5. the preparation technology of carbocisteine as claimed in claim 1, it is characterised in that: in described step (c), regulation system
PH to 7.5.
6. the preparation technology of carbocisteine as claimed in claim 1, it is characterised in that: in described step (c), the response time is
30-120 minute.
7. the preparation technology of carbocisteine as claimed in claim 1, it is characterised in that: in described step (d), use activated carbon
Carry out decolouring, adsorbing contaminant processes.
8. the preparation technology of carbocisteine as claimed in claim 7, it is characterised in that: in described step (d), decolour, adsorb
Impurity treatment controls the temperature of system and is 75-80 DEG C.
9. the preparation technology of carbocisteine as claimed in claim 1, it is characterised in that: in described step (e), regulation filtrate
PH process is time-consumingly not more than 30 minutes.
10. the preparation technology of carbocisteine as claimed in claim 1, it is characterised in that: also include crystallizing step (e) gained
With dissolving with hydrochloric acid, regulate the PH to 0.5-1.0 of this solution, carry out decolouring, adsorbing contaminant processes, filter, and regulate the PH of filtrate
To 2.8-3.0, cooling obtains carbocisteine crystallization again.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106680386A (en) * | 2016-12-07 | 2017-05-17 | 万全万特制药（厦门）有限公司 | Method for separating and testing related substance of carbocisteine raw material medicine and preparation by using liquid chromatography |
| CN109053508A (en) * | 2018-09-19 | 2018-12-21 | 山西云鹏制药有限公司 | A kind of preparation method of carbocisteine |
| CN110452142A (en) * | 2019-09-10 | 2019-11-15 | 云鹏医药集团有限公司 | A kind of preparation method of high-purity S- (carboxymethyl)-cysteine |
| CN111138326A (en) * | 2019-12-31 | 2020-05-12 | 宁波市远发生物工程有限公司 | Preparation method of S-carboxymethyl-L-cysteine |
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
| CN114366731A (en) * | 2022-02-10 | 2022-04-19 | 王有仁 | Application of carboxymethyl cysteine crystal in preparation of enzyme activity activator |
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| CN100371320C (en) * | 1998-06-29 | 2008-02-27 | 弗·哈夫曼-拉罗切有限公司 | Process for preparing s-aryl-semi-cystine and its derivatives |
| CN103102294A (en) * | 2012-03-28 | 2013-05-15 | 新沂市汉菱生物工程有限公司 | Production method carboxymethyl cysteine |
| CN105418471A (en) * | 2015-12-24 | 2016-03-23 | 宜昌三峡制药有限公司 | Synthetic method of carbocisteine |
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| US4129593A (en) * | 1976-10-19 | 1978-12-12 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Process for the production of high purity S-carboxymethyl-L-cysteine |
| CN100371320C (en) * | 1998-06-29 | 2008-02-27 | 弗·哈夫曼-拉罗切有限公司 | Process for preparing s-aryl-semi-cystine and its derivatives |
| CN103102294A (en) * | 2012-03-28 | 2013-05-15 | 新沂市汉菱生物工程有限公司 | Production method carboxymethyl cysteine |
| CN105418471A (en) * | 2015-12-24 | 2016-03-23 | 宜昌三峡制药有限公司 | Synthetic method of carbocisteine |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106680386A (en) * | 2016-12-07 | 2017-05-17 | 万全万特制药（厦门）有限公司 | Method for separating and testing related substance of carbocisteine raw material medicine and preparation by using liquid chromatography |
| CN109053508A (en) * | 2018-09-19 | 2018-12-21 | 山西云鹏制药有限公司 | A kind of preparation method of carbocisteine |
| CN110452142A (en) * | 2019-09-10 | 2019-11-15 | 云鹏医药集团有限公司 | A kind of preparation method of high-purity S- (carboxymethyl)-cysteine |
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
| CN114746399A (en) * | 2019-11-29 | 2022-07-12 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN114746399B (en) * | 2019-11-29 | 2024-05-24 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN111138326A (en) * | 2019-12-31 | 2020-05-12 | 宁波市远发生物工程有限公司 | Preparation method of S-carboxymethyl-L-cysteine |
| CN114366731A (en) * | 2022-02-10 | 2022-04-19 | 王有仁 | Application of carboxymethyl cysteine crystal in preparation of enzyme activity activator |
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| Publication number | Publication date |
|---|---|
| CN106083673B (en) | 2017-11-03 |
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