CN112778167A - Method for rapidly preparing N-benzenesulfonyl amino acid ester compound - Google Patents
Method for rapidly preparing N-benzenesulfonyl amino acid ester compound Download PDFInfo
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- CN112778167A CN112778167A CN201911061404.0A CN201911061404A CN112778167A CN 112778167 A CN112778167 A CN 112778167A CN 201911061404 A CN201911061404 A CN 201911061404A CN 112778167 A CN112778167 A CN 112778167A
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- C07—ORGANIC CHEMISTRY
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/16—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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Abstract
The invention discloses a rapid preparation methodN-benzenesulfonyl amino acid ester compounds; the present invention relates generally to chemical synthesis. The invention adopts a two-step one-pot strategy, takes substituted benzenethiol as a raw material, and can be obtained by reacting in-situ generated benzenesulfonyl chloride with hydrochloride of amino acid esterNThe benzenesulfonyl amino acid ester compound has the advantages of mild strategy conditions, high yield and high reaction efficiency, and can be used for quickly preparing the compound shown in the formula (I) and derivatives or analogues thereof. One of the fast preparation methods of the inventionNThe method for preparing the-benzenesulfonyl amino acid ester compound is simple to operate, mild in condition, high in yield and efficiency and high in application value.
Description
Technical Field
The invention relates to chemical synthesis technology; more particularly, the invention relates to a rapid preparationNA method for preparing the benzenesulfonyl amino acid ester compound.
Background
It has been found in recent studies that,N-benzenesulfonyl amino acid ester compounds can enhance stress tolerance of plants and can be used to increase plant growth and/or increase plant yield (CN 103491776A, WO2012/089722 a 2); and isNThe benzenesulfonyl amino acid fragment is widely present in bioactive molecules and drug molecules, and is a class and key intermediate thereof. However, the most common method at present is to prepare the benzene sulfonyl chloride and the amino acid ester hydrochloride as raw materials under the action of an acid-binding agent, but the reaction time of the method is too long, so that the method is not favorable for high-efficiency and high-yield synthesis.
Thus, development of rapid preparationNThe method for preparing the benzenesulfonyl amino acid ester compound has wide practical value and economic value.
Disclosure of Invention
In order to overcome the disadvantages, the pairNThe invention provides a systematic research of a synthesis method of a-benzenesulfonyl amino acid ester compound, and provides a rapid preparation methodNThe method for preparing the benzenesulfonyl amino acid ester compound realizes a two-step one-pot preparation method, improves the reaction efficiency and the yield, and has mild reaction conditions and simple and convenient operation.
In order to achieve the above object, the present invention provides a rapid preparation methodNThe method for preparing the benzenesulfonyl amino acid ester compound is mainly characterized in that a two-step one-pot strategy is adopted, substituted benzenethiol is used as a raw material, and benzenesulfonyl chloride generated in situ reacts with hydrochloride of amino acid ester to obtain the benzenesulfonyl amino acid ester compoundN-benzenesulfonyl amino acid ester compounds, the preparation strategy being mainly characterized by:
further, in the above technical solution, the combination of the oxidative chlorination reagents is selected from one or more of sodium hypochlorite/hydrochloric acid, thionyl chloride/hydrogen peroxide, sulfone chloride/hydrogen peroxide, phosphorus oxychloride/hydrogen peroxide, sodium chlorite/hydrochloric acid, sodium chlorate/hydrochloric acid, chlorine, chlorosulfonic acid, and zirconium chloride/hydrogen peroxide.
Further, in the above technical scheme, the acid-binding agent is selected from pyridine, and sodium chloride,N-methylmorpholine, triethylamine,N,N-one or more of diisopropylethylamine, potassium carbonate, sodium bicarbonate.
Further, in the above technical scheme, the molar ratio of the raw material substituted benzenethiol to the chlorinating agent combination is 1:1-1: 3; the molar ratio of the raw material 4-methylbenzyl mercaptan to the acid-binding agent is 1:4-1: 9.
Further, in the technical scheme, the temperature of the oxidation chlorination reaction is 0-50 ℃; the reaction temperature for constructing the sulfamide is 0-50 ℃.
Furthermore, the technical scheme is also suitable for C1-C3Alkyl of (C)1-C3The thiophenols of various positions and with various numbers of substitution of the alkoxy, cyano, nitro, ester and halogen groups are oxidatively chlorinated and reacted with the hydrochloride of the amino acid ester to prepare the derivatives and analogs of formula (I).
Compared with the prior art, the technical scheme of the invention has the beneficial effects that:
1. two-step one-pot strategy for preparing high-efficiency and high-yieldN-benzenesulfonyl amino acid esters.
2. The reaction raw materials are wide in source, and the oxidation chlorination reagent and the acid-binding agent are easy to obtain.
3. This strategy can be used to rapidly prepare derivatives of the structure shown in formula (I).
The inventors of the present invention found for the first time a rapid preparationNThe method of the-benzenesulfonyl amino acid ester compound has higher application value.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
FIG. 1 is a two-step one-pot preparationN-benzenesulfonyl amino acid ester compounds.
Detailed Description
The following describes in detail embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The invention provides a rapid preparation methodNA method for preparing the benzenesulfonyl amino acid ester compound, wherein the preparation strategy of the two-step one-pot method is as follows:
detailed description of the preferred embodiment 1
Two steps are onePot preparation of compound 4: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), glycine methyl ester hydrochloride and 8 equivalents of acetonitrile solution of acid-binding agent such as triethylamine are slowly dripped, after the reaction is completed (5 minutes), acid washing and drying are carried out, and then the compound 4 can be obtained by recrystallization or column chromatography, wherein the nuclear magnetic data are as follows1H NMR (600 MHz, CDCl3) δ7.74 (d, J = 8.4 Hz, 2H), 7.66 (d, J = 8.4 Hz, 2H), 5.17 (s, 1H), 3.81 (d, J = 5.4 Hz, 2H), 3.67 (s, 3H); 13C NMR (150 MHz, CDCl3) δ 169.18, 138.33, 132.31, 128.67, 127.82, 52.61, 43.88. The reaction equation is:
specific example 2
Compound 5 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding a solution of serine methyl ester hydrochloride and 8 equivalents of an acid-binding agent such as triethylamine in acetonitrile, after the reaction is completed (5 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 5, wherein the nuclear magnetic data are as follows1H NMR (600 MHz, CDCl3) δ7.74 (d, J = 8.4 Hz, 2H), 7.66 (d, J = 7.2 Hz, 2H), 5.91 (d, J = 7.8 Hz, 1H), 4.00 (s, 1H), 3.96–3.86 (m, 2H), 3.64 (s, 3H)。
Specific example 3
Compound 6 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completed (4 min) by monitoring on a point plate, slowly dropwise adding a solution of valine methyl ester hydrochloride and 8 equivalents of an acid-binding agent such as triethylamine in acetonitrile, after the reaction is completed (5 min), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 6, the nucleus of which isMagnetic data are as follows1H NMR (600 MHz, CDCl3) δ7.69 (d, J = 8.4 Hz, 2H), 7.64 (d, J = 8.4 Hz, 2H), 5.14 (d, J = 10.2 Hz, 1H), 3.74 (m, 1H), 2.05 (d, J = 6.0 Hz, 1H), 0.96 (d, J = 6.6 Hz, 3H), 0.87 (d, J = 6.6 Hz, 3H)。
Specific example 4
Compound 7 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding methyl methionine hydrochloride and 8 equivalents of acid-binding agent such as acetonitrile solution of triethylamine, after the reaction is completed (5 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 7, wherein the nuclear magnetic data are as follows1H NMR (600 MHz, DMSO-d 6) δ8.55 (d, J = 8.4 Hz, 1H), 7.81 (m, 2H), 7.68 (d, J = 8.4 Hz, 2H), 3.97 (d, J = 4.8 Hz, 1H), 3.44 (s, 3H), 2.45–2.36 (m, 1H), 2.31 (m, 1H), 1.95 (d, J = 7.2 Hz, 3H), 1.87–1.79 (m, 1H), 1.78–1.69 (m, 1H)。
Specific example 5
Compound 8 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding methyl aspartate hydrochloride and 8 equivalents of an acetonitrile solution of an acid-binding agent such as triethylamine, after the reaction is completed (5 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 8, wherein nuclear magnetic data of the compound are as follows1H NMR (600 MHz, DMSO) δ 8.65 (d, J = 9.0 Hz, 1H), 7.82 (d, J = 7.8 Hz, 2H), 7.69 (d, J = 7.8 Hz, 2H), 4.21 (q, J = 7.2 Hz, 1H), 3.52 (s, 3H), 3.42 (s, 3H), 2.74 (dd, J = 16.2, 6.0 Hz, 1H), 2.61 (dd, J = 16.2, 7.2 Hz, 1H)。
Specific example 6
Compound 9 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding phenylalanine methyl ester hydrochloride and 8 equivalents of acetonitrile solution of acid-binding agent such as triethylamine, after the reaction is completed (10 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 9, wherein the nuclear magnetic data are as follows1H NMR (600 MHz, DMSO-d 6) δ 8.68 (d, J = 9.0 Hz, 1H), 7.66 (d, J = 8.4 Hz, 2H), 7.49 (d, J = 8.4 Hz, 2H), 7.20 (d, J = 6.0 Hz, 3H), 7.12 (d, J = 7.2 Hz, 2H), 4.00 (m, 1H), 3.41 (s, 3H), 2.95 (m, 1H), 2.78 (m, 1H)。
Specific example 7
Compound 10 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding an acetonitrile solution of tyrosine methyl ester hydrochloride and 8 equivalents of an acid-binding agent such as triethylamine, after the reaction is completed (10 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 10, wherein nuclear magnetic data of the compound are as follows1H NMR (600 MHz, DMSO-d 6) δ 10.84 (s, 1H), 8.63 (d, J = 8.4 Hz, 1H), 7.56 (d, J = 7.8 Hz, 2H), 7.43 (d, J = 7.8 Hz, 2H), 7.30 (d, J = 7.8 Hz, 1H), 7.26 (d, J = 7.8 Hz, 1H), 7.08 (s, 1H), 7.05 (t, J = 7.2 Hz, 1H), 6.93 (t, J = 7.2 Hz, 1H), 3.97 (d, J = 7.2 Hz, 1H), 3.39 (s, 3H), 3.06 (m, 1H), 2.95–2.82 (m, 1H)。
Specific example 8
Compound 11 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding proline methyl ester hydrochloride and 8 equivalents of acid-binding agent such as acetonitrile solution of triethylamine, after the reaction is completed (5 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 11, wherein nuclear magnetic data of the compound are as follows1H NMR (600 MHz, CDCl3) δ7.75 (d, J = 8.4 Hz, 2H), 7.67 (d, J = 8.4 Hz, 2H), 4.35 (m, 1H), 3.72 (s, 3H), 3.46 (m, 1H), 3.39–3.30 (m, 1H), 2.13–2.06 (m, 1H), 2.06–1.94 (m, 2H), 1.88–1.79 (m, 1H)。
Specific example 9
Compound 12 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding methionine ethyl ester hydrochloride and 8 equivalents of acid-binding agent such as acetonitrile solution of triethylamine, after the reaction is completed (5 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 12, wherein the nuclear magnetic data are as follows1H NMR (600 MHz, CDCl3) δ 7.72 (d, J = 8.4 Hz, 2H), 7.65 (d, J = 8.4 Hz, 2H), 5.37 (d, J = 8.4 Hz, 1H), 4.05 (s, 1H), 4.00 (q, J = 7.2 Hz, 2H), 2.64–2.51 (m, 2H), 2.08 (s, 3H), 2.07–2.00 (m, 1H), 1.91 (dt, J = 13.8, 6.6 Hz, 1H), 1.14 (t, J = 7.2 Hz, 3H)。
Detailed description of example 10
Compound 13 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction is completely monitored by a point plate (4 minutes), slowly dropwise adding a solution of methionine benzyl ester hydrochloride and 8 equivalents of an acid-binding agent such as triethylamine in acetonitrile, after the reaction is completed (5 minutes), carrying out acid washing and drying, and further carrying out recrystallization or column chromatography to obtain a compound 13, wherein the nuclear magnetic data of the compound are as follows1H NMR (600 MHz, DMSO) δ8.60 (s, 1H), 7.75 (d, J = 8.4 Hz, 2H), 7.67 (d, J = 8.4 Hz, 2H), 7.37 (dd, J = 13.8, 6.0 Hz, 3H), 7.27 (d, J = 7.2 Hz, 2H), 4.95 (s, 2H), 4.03 (d, J = 5.4 Hz, 1H), 2.38 (dt, J = 13.2, 6.6 Hz, 1H), 2.33–2.25 (m, 1H), 1.91 (s, 3H), 1.85 (td, J = 13.2, 7.2 Hz, 1H), 1.76 (td, J = 14.4, 8.2 Hz, 1H)。
Specific example 11
Compound 14 was prepared in a two-step one-pot process: adding 4-bromobenzenethiol to acetonitrile, and then adding an oxidative chlorination reagent such as H2O2/SOCl2After the reaction was completed (4 minutes) by spotting the plate, the mixture was slowly droppedβAlanine methyl ester hydrochloride and 8 equivalents of an acid-binding agent such as triethylamine in acetonitrile, after reaction (5 minutes), acid washing and drying, and further recrystallization or column chromatography to obtain compound 14, wherein the nuclear magnetic data are as follows1H NMR (600 MHz, CDCl3) δ7.73 (d, J = 8.4 Hz, 2H), 7.67 (d, J = 8.4 Hz, 2H), 5.30 (t, J = 6.6 Hz, 1H), 3.68 (s, 3H), 3.21 (m, 2H), 2.57 (t, J = 6.0 Hz, 2H)。
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the technical features described in the above embodiments can be combined in an appropriate manner without contradiction, and various possible combinations are not described in the present invention in order to avoid unnecessary repetition.
Claims (7)
1. Rapid preparationNThe method for preparing the-benzenesulfonyl amino acid ester compound is mainly characterized in that a two-step one-pot strategy is adopted, substituted benzenethiol is used as a raw material, substituted benzenesulfonyl chloride is prepared by oxidation chlorination, and the substituted benzenesulfonyl chloride is reacted with hydrochloride of amino acid ester in situ to obtain the benzenesulfonyl amino acid ester compound with high efficiency and high yieldN-benzenesulfonyl amino acid ester compound, the preparation strategy is as follows:
wherein:
the above reaction is also suitable for the preparation of derivatives and analogues of formula (I).
2. A rapid preparation according to claim 1N-benzeneThe method for preparing the sulfonyl amino acid ester compound comprises the step of combining an oxidation chlorination reagent with one or more of sodium hypochlorite/hydrochloric acid, thionyl chloride/hydrogen peroxide, sulfone chloride/hydrogen peroxide, phosphorus oxychloride/hydrogen peroxide, sodium chlorite/hydrochloric acid, sodium chlorate/hydrochloric acid, chlorine, chlorosulfonic acid and zirconium chloride/hydrogen peroxide.
3. The method of claim 1, wherein the acid-binding agent is selected from the group consisting of pyridine, and pyridine,N-methylmorpholine, triethylamine,N,N-one or more of diisopropylethylamine, potassium carbonate, sodium bicarbonate.
4. The method for rapid preparation of an abscisic acid receptor agonist as claimed in claim 1, wherein the molar ratio of the starting substituted benzenethiol to the oxidative chlorination reagent combination is 1:1-1: 4; the molar ratio of the raw material substituted benzenethiol to the acid-binding agent is 1:4-1: 9.
5. The method for rapidly preparing an abscisic acid receptor agonist as defined in claim 1, wherein the temperature of the oxidative chlorination reaction is 0-50 ℃; the reaction temperature for constructing the sulfamide is 0-50 ℃.
6. The method for rapidly preparing an abscisic acid receptor agonist as claimed in claim 1, wherein the same applies to C1-C3Alkyl of (C)1-C3The thiophenols with different positions and different substitution numbers of alkoxy, cyano, nitro, ester group and halogen are oxidized and chlorinated and then react with amino acid ester hydrochloride to prepare the derivatives and analogs shown in the formula (I).
7. The rapid preparation method according to claim 1 to 6, wherein,Nthe benzenesulfonyl amino acid ester compounds, the derivatives and the analogues thereof can be prepared by adopting a one-pot method strategy.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1334726A (en) * | 1998-12-16 | 2002-02-06 | 史密丝克莱恩比彻姆公司 | Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists |
| CN1612729A (en) * | 2001-11-20 | 2005-05-04 | 冬姆佩股份公司 | 2-aryl-propionic acid and medicine composition containing same |
| CN109678797A (en) * | 2018-08-17 | 2019-04-26 | 邵阳学院 | A method of quickly preparing ABA Receptor agonist |
-
2019
- 2019-11-01 CN CN201911061404.0A patent/CN112778167A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1334726A (en) * | 1998-12-16 | 2002-02-06 | 史密丝克莱恩比彻姆公司 | Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists |
| CN1612729A (en) * | 2001-11-20 | 2005-05-04 | 冬姆佩股份公司 | 2-aryl-propionic acid and medicine composition containing same |
| CN109678797A (en) * | 2018-08-17 | 2019-04-26 | 邵阳学院 | A method of quickly preparing ABA Receptor agonist |
Non-Patent Citations (2)
| Title |
|---|
| DAVID CRICH等: ""Triblock Peptide and Peptide Thioester Synthesis With Reactivity-Differentiated Sulfonamides and Peptidyl Thioacids"", 《ANGEW. CHEM. INT. ED.》 * |
| KIUMARS BAHRAMI等: ""Direct Conversion of Thiols to Sulfonyl Chlorides and Sulfonamides"", 《J. ORG. CHEM.》 * |
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