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Method of preparing (S)-(-)-2-chloropropionate and (R)-(+)-2-chloro propionic acid

A technology of chloropropionic acid ester and chloropropionic acid is applied in chemical instruments and methods, preparation of carboxylic acid esters, preparation of organic compounds, etc., and can solve the problems of affecting splitting effect, low splitting yield and high production cost, Achieve the effect of low production cost, simple reaction process and high selectivity

Inactive Publication Date: 2008-11-26
ZHEJIANG UNIV OF TECH
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  • Abstract
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  • Claims
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AI Technical Summary

Problems solved by technology

[0004] In the above-mentioned method, when optically pure 2-chloropropionic acid (ester) is prepared by the chemical resolution method, the optically pure resolution reagent of stoichiometry is often needed, and the optically pure resolution reagent is relatively expensive, and the resolution yield is relatively low, so that The production cost is higher; when asymmetrically synthesizing optically pure 2-chloropropionic acid (ester), chiral raw materials are required; biological enzymatic method splits 2-chloropropionic acid (ester) to prepare optically pure 2-chloropropionic acid (ester) ) has the advantages of mild reaction conditions and simple post-treatment, but the source and type of biological enzyme catalysts significantly affect the resolution effect. In order to obtain 2-chloropropionic acid (ester) optical isomers with high optical purity, its resolution Yields tend to be lower

Method used

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  • Method of preparing (S)-(-)-2-chloropropionate and (R)-(+)-2-chloro propionic acid
  • Method of preparing (S)-(-)-2-chloropropionate and (R)-(+)-2-chloro propionic acid
  • Method of preparing (S)-(-)-2-chloropropionate and (R)-(+)-2-chloro propionic acid

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Experimental program
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Effect test

Embodiment 1～4

[0021] Add a certain amount of racemic 2-chloropropionate into a 500mL flask, 250mL 0.1mol / L disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution (pH=7.2), 1.0g of porcine pancreatic lipase, at 30°C Stir the reaction for a certain period of time. After the reaction, centrifuge to remove porcine pancreatic lipase, extract the reaction solution with dichloromethane, dry the organic layer over anhydrous sodium sulfate, and distill under reduced pressure to remove the organic solvent to obtain (S)-(-)-2-chloropropane Ester; the aqueous layer was acidified to pH less than or equal to 1.0 and extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, and the organic solvent was removed by vacuum distillation to obtain (R)-(+)-2-chloropropionic acid . The product yield and enantiomeric excess value determination results are listed in Table 1.

[0022] Table 1: Resolution results of different 2-chloropropionates

[0023]

[0024...

Embodiment 5

[0026] In a 500mL flask, add 8.23g of racemic butyl 2-chloropropionate, 250mL of 0.1mol / L disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution (pH=7.2), 1.0g of porcine pancreatic lipase, at 25°C The reaction was stirred for 14 hours. After the reaction, centrifuge to remove porcine pancreatic lipase, extract the reaction solution with dichloromethane, dry the organic layer over anhydrous sodium sulfate, and distill under reduced pressure to remove the organic solvent to obtain (S)-(-)-2-chloropropane Butyl acid 3.9 g (94.8% yield, 89% enantiomeric excess).

Embodiment 6

[0028] In a 500mL flask, add 4.12g of racemic butyl 2-chloropropionate, 250mL 0.1mol / L disodium hydrogen phosphate-sodium dihydrogen phosphate buffer solution (pH=7.2), 1.0g of porcine pancreatic lipase, at 30 The reaction was stirred at °C for 10 hours. After the reaction, centrifuge to remove porcine pancreatic lipase, extract the reaction solution with dichloromethane, dry the organic layer over anhydrous sodium sulfate, and distill under reduced pressure to remove the organic solvent (S)-(-)-2-chloropropionic acid Butyl ester 1.7 g (82.5% yield, 88.6% enantiomeric excess).

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Abstract

A process for preparing (S)-(-)-2-chloropropionate and (R)-(+)-2-chloropropionic acid includes such steps as selective hydrolytic reaction of dl-2-chloropropionate in reaction medium under existence of pig steapsase, and separating two products from the resultant liquid.

Description

(1) Technical field [0001] The invention relates to a method for preparing (S)-(-)-2-chloropropionate and (R)-(+)-2-chloropropionic acid. (2) Background technology [0002] 2-chloropropionic acid (ester) is an important raw material for the synthesis of pesticides, dyes and medicines. Its application involves many sectors of the national economy and people's daily life. It is an important fine chemical product. Especially (S)-(-)2-chloropropionic acid (ester) is a key intermediate for the synthesis of highly efficient and low-toxic aryloxypropionic acid herbicides, as it can be used for the synthesis of (R)-2-(4 -Hydroxyphenoxy)propionic acid (ester) intermediate, fenzafop-p-ethyl, fluazifop-p-ethyl, etc. [0003] At present, the preparation methods of (S)-(-)-2-chloropropionic acid (ester) and (R)-(+)-2-chloropropionic acid (ester) include: (1) chemical resolution; (2) ) enzymatic resolution; (3) chromatographic resolution; (4) asymmetric synthesis, etc. For example: JP ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/63C07C67/00C07C53/19C07C51/09
Inventor 施介华金迪
Owner ZHEJIANG UNIV OF TECH
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