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Method of preparing antimer pure parahydroxy phenyl glycine

A technology of p-hydroxyphenylglycine and p-hydroxyphenylglycine methyl ester, which is applied in fermentation and other fields, can solve the problems of nitrous acid environmental pollution and expensive enzymes, and achieve low environmental pollution, simple and easy-to-control reaction process, and mild reaction conditions Effect

Inactive Publication Date: 2006-09-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has been widely adopted, but the enzymes used are expensive, and the use of nitrous acid brings serious environmental pollution problems.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 4ml containing 0% (v / v) ionic liquid BMIM·BF 4 / Phosphate buffer (50mmol / L, pH 7.0) mixed system is put into the Erlenmeyer flask with stopper and mixed evenly, then add 0.4mmol p-hydroxyphenylglycine methyl ester and 300mg papain (1.2units / mg), under normal pressure , placed in a 40°C, 160rev. / min water bath constant temperature oscillator, reacted for 24h, added ethyl acetate, extracted the remaining unreacted D-hydroxyphenylglycine methyl ester, vacuum distilled, in NaOH (1.0mol / L) in aqueous solution to hydrolyze into D-p-hydroxyphenylglycine; add concentrated hydrochloric acid (8.0mol / L) to the ionic liquid / water mixed system, the pH value drops to about 2.0, after shaking for several minutes, the product L-p-hydroxyphenyl Glycine was precipitated, filtered and dried to obtain enantiomerically pure p-hydroxyphenylglycine with a yield of 38.5% and enantiomeric purity of 95%.

Embodiment 2

[0021] 4ml containing 10% (v / v) ionic liquid BMIM·BF 4 / Phosphate buffer (50mmol / L, pH7.0) mixed system is put into the Erlenmeyer flask with stopper and mixed evenly, then add 0.4mmol p-hydroxyphenylglycine methyl ester and 300mg papain (1.2units / mg), under normal pressure placed in a constant temperature oscillator in a water bath at 40°C and 160 rev. / min, and reacted for 24 hours, the yield of L-p-hydroxyphenylglycine was 44.7%, and the enantiomeric purity was 95.1%.

Embodiment 3

[0023] 4ml containing 12.5% ​​(v / v) ionic liquid BMIM·BF 4 / Phosphate buffer (50mmol / L, pH7.0) mixed system is put into the Erlenmeyer flask with stopper and mixed evenly, then add 0.4mmol p-hydroxyphenylglycine methyl ester and 300mg papain (1.2units / mg), under normal pressure placed in a water bath constant temperature oscillator at 40°C and 160 rev. / min, and reacted for 24 hours, the yield of L-p-hydroxyphenylglycine was separated to be 47.2%, and the enantiomeric purity was 95.7%.

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PUM

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Abstract

A process for preparing the high-purity antimer, L-p-hydroxyphenyl glycine includes such steps as sequentially adding ionic liquid BMIM.BF4, phosphoric acid buffer, methyl p-hydroxyphenylglycenate, and papain, reacting, ultrafilter to remove suspended particles and enzyme, and separating to obtain L-p-hydroxyphenyl glycine.

Description

technical field [0001] The present invention relates to a new method for preparing enantiomerically pure p-hydroxyphenylglycine. Background technique [0002] Enantiomerically pure p-hydroxyphenylglycine is an important side chain of semi-synthetic β-lactam antibiotics, used in the synthesis of amoxicillin, cefadroxil, cefoperazone, cefurozil and cefadroxol, etc. At present, the production of enantiomerically pure p-hydroxyphenylglycine mostly adopts the following two methods at home and abroad: one is to synthesize racemic p-hydroxyphenylglycine with p-oxybenzoic acid method, p-hydroxybenzaldehyde method or glyoxylic acid method, Then the racemate is separated; the synthesis process of the racemate is mature, and the resolution of the racemate is a key step with great technical difficulty. So far, the methods for splitting p-hydroxyphenylglycine include chemical method, induced crystallization method and enzymatic method. Among them, chemical method and crystallization met...

Claims

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Application Information

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IPC IPC(8): C12P13/04
Inventor 宗敏华娄文勇许若
Owner SOUTH CHINA UNIV OF TECH
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