CN103739635B - A kind of purification process of mannose triflate intermediate - Google Patents
A kind of purification process of mannose triflate intermediate Download PDFInfo
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Abstract
The invention provides a kind of purification process of mannose triflate intermediate, comprise the steps: to get 1, 3, 4, 6-is tetra-acetylated-and β-D-MANNOSE crude product is added in the mixing material containing n-butanol and glycol monoethyl ether, be heated to dissolve, be cooled to crystallization complete, filter, washing, dry, obtain mannose triflate intermediate 1, 3, 4, 6-is tetra-acetylated-β-D-MANNOSE crystal, improve significantly 1, 3, 4, 6-is tetra-acetylated-yield and the purity of β-D-MANNOSE, thereby solve synthetic mannose triflate intermediate 1 in prior art, 3, 4, 6-is tetra-acetylated-yield and the not high problem of purity of β-D-MANNOSE.
Description
Technical field
The invention belongs to separation and purification field, be specifically related to a kind of mannose triflate intermediate, 1,3,4,6-tetrem acylThe purification process of base-β-D-MANNOSE.
Background technology
The chemical name of mannose triflate is 1,3,4,6-, tetra--O-acetyl group-2-O-trifyl-β-D-sweet dewSugar is synthetic PET developer18The precursor of F-FDG. At present,18F-FDG uses in positron emission fault (PET) video pictureTracer widely, is not only widely used in laboratory research, but also is widely used in the day of cardiovascular, nerve and tumour etc.Normal clinical diagnosis, its use has accounted for the more than 90% of PET video picture clinical practice, thereby makes the demand of mannose triflateIncrease, thereby the productive rate to mannose triflate synthetic in prior art and purity need to propose higher requirement to meet trifluoroThe great demand amount of mannose.
At present, the industrial production of mannose triflate relates to multistep chemical synthesis, optimizes each synthesis step for costProductive rate and the purity of reduction and mannose triflate are all most important, and the yield and the purity that improve intermediate can make final productProductive rate, the purity of thing mannose triflate all improve greatly, and improve yield and the purity of reaction intermediate, particularly syntheticReaction intermediate yield and the purity in later stage, for the quality pipe that meets for example mannose triflate described in European Pharmacopoeia is providedReason specification standards are extremely important, and the final medicine meeting described in American Pharmacopeia for example providing is be provided simultaneously18F-FDG(2-18F-2-deoxy-D-glucose) quality management specification standards also extremely important.
But in the prior art mannose triflate synthetic, greatly mainly with 1,3,4,6-tetra-acetylated-β-D-MANNOSE isIntermediate carries out the synthetic reaction in later stage, and therefore 1,3,4,6-is tetra-acetylated-and the yield of β-D-MANNOSE and purity is for productThe productive rate of mannose triflate, the impact of purity are even more important.
The synthetic method of disclosed mannose triflate in prior art, as Russ P document RU2165266C1, Yang ZhiThe paper that the people such as " synthesizing of diagnostic reagent mannose triflate " and TatsushiToyokuni that outstanding person delivers delivers《PracticalandReliableSynthesisof1,3,4,6-Tetra-O-acetyl-2-Otrifluoromethanesulfonyl-β-D-mannopyranose,aPrecursorof2-Deoxy-2-[18F]Fluoro-D-glucose (FDG) ", wherein the synthetic method of disclosed mannose triflate mainly contains three kinds, and these three kinds of methods are equalBy reaction intermediate 1,3,4,6-is tetra-acetylated-and β-D-MANNOSE (1) makes with equimolar TFMS anhydride reactant, reactionEquation is as follows:
For above-mentioned intermediate-1,3,4,6-is tetra-acetylated-β-D-MANNOSE synthetic, TatsushiToyokuni etc.Paper " PracticalandReliableSynthesisof1,3,4,6-Tetra-O-acetyl-that people delivered in 20042-Otrifluoromethanesulfonyl-β-D-mannopyranose,aPrecursorof2-Deoxy-2-[18F]Fluoro-D-glucose (FDG) " in, disclose 1,3,4,6-tetra-acetylated-β-D-MANNOSE (1) is taking D-MANNOSE as formerMaterial, through acetylation, bromo, cyclization, then generates with hydrochloric acid hydrolysis, and reaction equation is as follows:
The hydrolysis of the 4th step in above-mentioned steps can produce two major impurities 2,3,4, and 6-is tetra-acetylated-β-D-Mannose (4) and 2,3,4,6-be tetra-acetylated-α-D-MANNOSE (5) (See Figure formula). Wherein, 2,3,4,6-tetra-acetylated-α-The unstable meeting of D-MANNOSE (5) is converted into 2,3,4,6-very soon tetra-acetylated-β-D-MANNOSE (4), in addition, 1,3,4,6-tetremAcyl-beta-D-MANNOSE (1) can be shifted and is gradually transformed into impurity (4) and (5) by acyl group.
Although in above-mentioned document, disclose 1,3,4,6-tetra-acetylated-β-D-MANNOSE (1) can pass through ethyl alcohol recrystallization,Be that its recrystallization yield is lower, only have less than 50%. For another example all public in Chinese patent literature CN1911947A and CN101659682AOpened 1,3,4,6-tetra-acetylated-synthesis step of β-D-MANNOSE (1), both adopt to add ether crystallization and then acquisition1,3,4 of certain yield and purity, 6-is tetra-acetylated-β-D-MANNOSE (1), but its acquisition 1,3,4,6-is tetra-acetylated-The yield of β-D-MANNOSE and purity are not high yet.
Summary of the invention
For this reason, technical problem to be solved by this invention is mannose triflate intermediate 1,3 synthetic in prior art,4,6-is tetra-acetylated-yield of β-D-MANNOSE and purity not high and then affect the productive rate of synthetic mannose triflate and purityProblem, so provide one can significantly improve 1,3,4,6-tetra-acetylated-yield of β-D-MANNOSE and the purifying side of purityMethod.
For solving the problems of the technologies described above, the invention provides a kind of 1,3,4,6-tetra-acetylated-the purifying side of β-D-MANNOSEMethod, comprises the steps,
Get synthetic obtain 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product is added to containing n-butanol and ethylene glycol list firstIn the mixing material of ether, be heated to dissolve, and it is complete to be cooled to subsequently crystallization, filters, washing, dry, obtain mannose triflateIntermediate 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
In the purification process of above-mentioned mannose triflate intermediate, the body of described n-butanol and described glycol monoethyl etherLong-pending than being 4-8:1.
In the purification process of above-mentioned mannose triflate intermediate, the body of described n-butanol and described glycol monoethyl etherLong-pending than being 6:1.
In the purification process of above-mentioned mannose triflate intermediate, described 1,3,4,6-is tetra-acetylated-β-D-MANNOSEThe volume ratio of the weight of crude product and the described mixing material containing n-butanol and glycol monoethyl ether is 1:5-15; Described weight withThe proportionate relationship of volume is the relation of g/mL.
In the purification process of above-mentioned mannose triflate intermediate, described 1,3,4,6-is tetra-acetylated-β-D-MANNOSEThe volume ratio of the weight of crude product and the described mixing material containing n-butanol and glycol monoethyl ether is 1:10.
In the purification process of above-mentioned mannose triflate intermediate, in the step of described decrease temperature crystalline, contain described in controlHave 1,3,4,6-tetra-acetylated-lysate of β-D-MANNOSE is cooled to 8-15 DEG C, is preferably cooled to 10 DEG C.
In the purification process of above-mentioned mannose triflate intermediate, in the crystal step that described washing leaches, to account for filterThe butanol solution repeated washing that the crystal weight 0.3-0.8 volume going out is doubly measured 2-3 time, preferred to account for the crystal weight leachingThe butanol solution repeated washing that 0.5 volume is doubly measured 2-3 time; The weight of described crystal and the volume of described butanol solution are doubly measuredPass be the relation of g/ml.
In the purification process of above-mentioned mannose triflate intermediate, in described drying steps, control after described washingCrystal is in 45-55 DEG C, vacuum drying 8-12 hour, preferably controls crystal after described washing little in 50 DEG C, vacuum drying 10Time.
The present invention by above-mentioned purification process make 1,3,4,6-tetra-acetylated-β-D-MANNOSE.
The purification process of mannose triflate intermediate of the present invention is being prepared mannose triflate and synthetic PET video pictureThe application in agent field.
Technique scheme of the present invention has the following advantages compared to existing technology:
(1) purification process of mannose triflate intermediate of the present invention, utilizes n-butanol and glycol monoethyl etherPure solution is mixed to get mixing material, and as recrystallisation solvent, to mannose triflate intermediate 1,3,4,6-is tetra-acetylated-β-D-is sweetReveal sugar and carry out purification, improved significantly 1,3,4,6-tetra-acetylated-yield and the purity of β-D-MANNOSE, average yieldReach 75.8%, purity, up to 99.5%, with respect to the yield of 40% left and right in prior art, has had significant raising, thereby solvesSynthetic mannose triflate intermediate 1,3,4 in prior art, 6-is tetra-acetylated-yield and the purity of β-D-MANNOSE is not highProblem, obtain by method of the present invention simultaneously 1,3,4,6-is tetra-acetylated-β-D-MANNOSE also has good stability, protectThe advantage that the matter phase is long;
(2) purification process of mannose triflate intermediate of the present invention, by controlling in mixing material, described positive fourthThe volume ratio of alcohol and glycol monoethyl ether is 4-8:1, significantly improved 1,3,4,6-tetra-acetylated-receipts of β-D-MANNOSERate and purity;
(3) purification process of mannose triflate intermediate of the present invention, by control 1,3,4,6-tetra-acetylated-β-The ratio of the volume of the weight of D-MANNOSE crude product and described n-butanol and glycol monoethyl ether mixed solution is 1:5-15, significantlyThe raising of degree 1,3,4,6-is tetra-acetylated-yield and the purity of β-D-MANNOSE;
(4) purification process of mannose triflate intermediate of the present invention can be widely used in preparing mannose triflateAnd PET developer18The fields such as F-FDG.
Detailed description of the invention
In following embodiment for the elaboration of the technique effect of purification process of the present invention, with disclosed in prior artMethod be example carry out 1,3,4,6-tetra-acetylated-preparation of β-D-MANNOSE, select according to published bibliography《PracticalandReliableSynthesisof1,3,4,6-Tetra-O-acetyl-2-Otrifluoromethanesulfonyl-β-D-mannopyranose,aPrecursorof2-Deoxy-2-[18F]Fluoro-D-glucose (FDG) " in the described synthetic method recorded be example, taking triacetyl dioxa glutinous rehmannia mannose as formerMaterial, obtains 1,3,4 of processing to be purified, and 6-is tetra-acetylated-β-D-MANNOSE crude product: by the triacetyl dioxa glutinous rehmannia sweet dew of 56gSugar (3) is dissolved in the acetone of 140mL, adds the HCl solution of the 1M of 33.6mL, and bath temperature is controlled at 18 DEG C of left and right. Room temperature is anti-Answer after 10 minutes, evaporate to dryness obtains white solid. Add the CHCl of 120mL3Dissolve this solid, then wash with the distilled water of 60mLThree times. Through anhydrous sodium sulfate drying, filter. Filtrate, through evaporate to dryness, obtains yellow oil. Add the ether of 60mL fully to stirMix, separate out white solid, suction filtration, vacuum drying, obtain 1,3,4,6-tetra-acetylated-β-D-MANNOSE crude product 14g, detect described thickImpurity content in product is 0.678g, mp:159-163 DEG C.
Embodiment 1
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, bagDraw together following steps:
In there-necked flask, add the described mixing material 50mL containing n-butanol and glycol monoethyl ether, described n-butanol andThe ratio of glycol monoethyl ether volume is 6:1, add above-mentioned make 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product 10g,And solution is heated to 80 DEG C, until 1,3,4,6-tetra-acetylated-β-D-MANNOSE crude product dissolves completely, subsequently by above-mentioned dissolvingLiquid is cooled to 8 DEG C, and standing crystallization 1 hour, filters the solution of above-mentioned crystallization, adds above-mentioned the leaching of 3mL butanol solution washingCrystal, repeated washing 2-3 time, by washing after crystal in 45 DEG C of vacuum drying 8 hours, obtain 1,3,4,6-tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 2
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, bagDraw together following steps:
In there-necked flask, add the described mixing material 100mL containing n-butanol and glycol monoethyl ether, described n-butanolWith the ratio of glycol monoethyl ether volume be 6:1, add above-mentioned make 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product10g, and solution is heated to 100 DEG C, until described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product dissolves completely, subsequentlyAbove-mentioned lysate is cooled to 10 DEG C, and standing crystallization 2 hours, filter the solution of above-mentioned crystallization, add 5mL butanol solution to washWash the above-mentioned crystal leaching, repeated washing 2-3 time, by the crystal after washing in 50 DEG C of vacuum drying 10 hours, obtain described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 3
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, bagDraw together following steps:
In there-necked flask, add the described mixing material 150mL containing n-butanol and glycol monoethyl ether, described n-butanolWith the ratio of glycol monoethyl ether volume be 6:1, add above-mentioned make 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product10g, and solution is heated to 110 DEG C, until described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product dissolves completely, subsequentlyAbove-mentioned lysate is cooled to 15 DEG C, and standing crystallization 3 hours, filter the solution of above-mentioned crystallization, add 7mL butanol solutionWash the above-mentioned crystal leaching, repeated washing 2-3 time, by the crystal after washing in 55 DEG C of vacuum drying 12 hours, obtain described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 4
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, bagDraw together following steps:
In there-necked flask, add the described mixing material 100mL containing n-butanol and glycol monoethyl ether, described n-butanolWith the ratio of glycol monoethyl ether volume be 4:1, add above-mentioned make 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product10g, and solution is heated to 100 DEG C, until described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product dissolves completely, subsequentlyAbove-mentioned lysate is cooled to 10 DEG C, and standing crystallization 2 hours, filter the solution of above-mentioned crystallization, add 5mL butanol solution to washWash the above-mentioned crystal leaching, repeated washing 2-3 time, by the crystal after washing in 50 DEG C of vacuum drying 10 hours, obtain described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Embodiment 5
Mannose triflate intermediate 1,3,4 described in the present embodiment, 6-is tetra-acetylated-purification process of β-D-MANNOSE, bagDraw together following steps:
In there-necked flask, add the described mixing material 50mL containing n-butanol and glycol monoethyl ether, described n-butanol andThe ratio of glycol monoethyl ether volume is 8:1, add above-mentioned make 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product 10g,And solution is heated to 100 DEG C, and until described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product dissolves completely, subsequently by upperState lysate and be cooled to 10 DEG C, and standing crystallization 2 hours, filter the solution of above-mentioned crystallization, add in the washing of 5mL butanol solutionState the crystal leaching, repeated washing 2-3 time, by the crystal after washing in 50 DEG C of vacuum drying 10 hours, obtain described 1,3,4,6-Tetra-acetylated-β-D-MANNOSE crystal.
Comparative example 1
The present embodiment described 1,3,4,6-is tetra-acetylated-purification process of β-D-MANNOSE and above-described embodiment 3 pureChange step basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is ethanol, obtain described 1,3,4,6-tetrem acylBase-β-D-MANNOSE crystal.
Comparative example 2
The present embodiment described 1,3,4,6-is tetra-acetylated-purification process of β-D-MANNOSE and above-described embodiment 3 pureChange step basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is ether, obtain described 1,3,4,6-tetrem acylBase-β-D-MANNOSE crystal.
Comparative example 3
The present embodiment described 1,3,4,6-is tetra-acetylated-purification process of β-D-MANNOSE and above-described embodiment 3 pureChange step basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is n-butanol, obtain described 1,3,4,6-tetremAcyl-beta-D-MANNOSE crystal.
Comparative example 4
The present embodiment described 1,3,4,6-is tetra-acetylated-purification process of β-D-MANNOSE and above-described embodiment 3 pureChange step basic identical, difference is only that the recrystallisation solvent adopting in the present embodiment is glycol monoethyl ether, obtain described 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
Effect example
To use in above-described embodiment 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crude product and embodiment 1-3, rightIn ratio 1-4, obtain through crystallization purifying 1,3,4,6-is tetra-acetylated-β-D-MANNOSE carries out HPLC analysis, described HPLC dividesAnalyse condition as follows: analytic type chromatographic column: C18Reverse-phase chromatographic column, particle diameter is 5um, pillar specification is 250*4.6mm, mobile phase compositionVolume ratio is acetonitrile: water=65:35, and running temperature is 25 DEG C, and flow velocity is for being 1.0L/min, and detection wavelength is 220nm, while going out peakBetween be 3.3min, detect describedly 1,3,4,6-is tetra-acetylated-purity of β-D-MANNOSE and the content of impurity, the purity obtainingOutcome record is in following table.
According to formula 1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal yield/1, and 3,4,6-is tetra-acetylated-β-D-sweet dewThe amount * 100% of sugar crude product, calculates described in each embodiment and comparative example 1,3,4, and 6-is tetra-acetylated-yield of β-D-MANNOSE,Wherein said 1,3,4,6-is tetra-acetylated-and the amount of β-D-MANNOSE crude product is 10g, and the yield outcome record obtaining is in following table.
The effect data of the each embodiment of table 1
Relatively found by the above results, purification process of the present invention obtain 1,3,4,6-is tetra-acetylated-β-D-MANNOSEYield on average reach 75.8%, purity on average reaches 99.5%, shows thus, purification process of the present invention has improved 1 significantly,3,4,6-is tetra-acetylated-yield and the purity of β-D-MANNOSE, thus solve in prior art in the middle of synthetic mannose triflateBody 1,3,4,6-is tetra-acetylated-yield and the not high problem of purity of β-D-MANNOSE.
Obviously above-described embodiment is only for example is clearly described, and the not restriction to embodiment. RightIn those of ordinary skill in the field, can also make on the basis of the above description other multi-form variation orVariation. Here without also giving exhaustive to all embodiments. And the apparent variation of being extended out thus orVariation is still among the protection domain in the invention.
Claims (7)
1. a purification process for mannose triflate intermediate, is characterized in that, comprises the steps:
Get 1,3,4,6-tetra-acetylated-β-D-MANNOSE crude product is added to n-butanol and the ethylene glycol list first that volume ratio is 4-8:1In the mixing material of ether, be heated to dissolve, and it is complete to be cooled to subsequently crystallization, filters, washing, dry, obtain mannose triflateIntermediate-1,3,4,6-is tetra-acetylated-β-D-MANNOSE crystal.
2. the purification process of mannose triflate intermediate according to claim 1, is characterized in that, described n-butanol and instituteThe volume ratio of stating glycol monoethyl ether is 6:1.
3. the purification process of mannose triflate intermediate according to claim 1 and 2, is characterized in that, described 1,3,4,6-is tetra-acetylated-weight of β-D-MANNOSE crude product and the volume ratio of the described mixing material containing n-butanol and glycol monoethyl etherFor 1:5-15; The proportionate relationship of described weight and volume is the relation of g/mL.
4. the purification process of mannose triflate intermediate according to claim 3, is characterized in that, described 1,3,4,6-tetra-The volume ratio of the weight of acetyl group-β-D-MANNOSE crude product and the described mixing material containing n-butanol and glycol monoethyl ether is 1:10。
5. according to the purification process of the mannose triflate intermediate described in claim 1 or 2 or 4, it is characterized in that described coolingIn the step of crystallization, contain described in control 1,3,4,6-tetra-acetylated-lysate of β-D-MANNOSE is cooled to 8-15 DEG C.
6. the purification process of mannose triflate intermediate according to claim 5, is characterized in that, described washing leachesIn crystal step, to account for butanol solution repeated washing 2-3 time that the 0.3-0.8 volume of the described crystal weight leaching doubly measures;The pass that the weight of described crystal and the volume of described butanol solution are doubly measured is the relation of g/mL.
7. according to the purification process of the mannose triflate intermediate described in claim 1 or 2 or 4 or 6, it is characterized in that, described inIn drying steps, control crystal after described washing in 45-55 DEG C, vacuum drying 8-12 hour.
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