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Method for splitting DL-p-hydroxymandelic acid

A technology of p-hydroxymandelic acid and a resolving agent is applied in the field of preparing high-purity D-p-hydroxymandelic acid, and can solve the problem that the splitting of DL-p-hydroxymandelic acid has little reference value, low product purity, and many operation steps. and other problems, to achieve the effect of high-efficiency splitting efficiency, low-cost solvent, and improved reaction yield

Inactive Publication Date: 2010-03-31
BAOWU CHARCOAL MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield is relatively low because half of the raw material is consumed
[0011] Compared with the above several processes, there are many problems such as many operation steps, long reaction time, low product purity, low yield, etc., which have little reference significance for the resolution of DL-p-hydroxymandelic acid

Method used

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  • Method for splitting DL-p-hydroxymandelic acid
  • Method for splitting DL-p-hydroxymandelic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Get DL-p-hydroxymandelic acid 8.4 grams (0.05mol), (S)-(+)-2-amino-4-phenylbutyric acid ethyl ester hydrochloride 12.18 grams (0.05mol), drop into 120ml 30% In ethanol aqueous solution, start stirring, N 2 Protect, heat up to 75°C to form a transparent reaction solution, then slowly add 2 grams (0.05mol) of sodium hydroxide, continue to stir the reaction for 30min, a white precipitate occurs, slowly cool down to 10°C, let the formed D- The double salt of p-hydroxymandelic acid is fully separated. Filtration under reduced pressure obtains filtrate A and 9.07 grams of white crystals, and yield is 97% of theoretical yield, and this white crystals is D-parahydroxymandelic acid double salt (D-parahydroxymandelic acid (S)-(+) -2-amino-4-phenylbutyric acid ethyl ester), washed with a small amount of ethanol, and dried in a vacuum oven.

[0051] Take by weighing 9.07 grams of dried D-p-hydroxymandelic acid (S)-(+)-2-amino-4-phenylbutyric acid ethyl ester 9.07 grams, be dissol...

Embodiment 2

[0055] Get (S)-(+)-2-amino-4-phenylbutyric acid ethyl ester hydrochloride 12.18 grams (0.05mol), drop into 120ml mass percent concentration and be 50% ethanol aqueous solution, start stirring, N 2 protection, the temperature was raised to 55° C., and then 2 g (0.05 mol) of sodium hydroxide was slowly added to form a transparent reaction solution. Then add 8.4 g (0.05 mol) of DL-p-hydroxymandelic acid, continue to stir the reaction for 80 minutes, a white precipitate occurs, slowly cool down to 10°C, and allow the formed D-p-hydroxymandelic acid double salt to be fully separated. 9.18 grams of white crystals obtained by filtration under reduced pressure and filtrate A, the yield is 98.2% of the theoretical yield, the white crystals are D-p-hydroxymandelic acid (S)-(+)-2-amino-4-benzene ethyl butyrate, washed with a small amount of ethanol, and dried in a vacuum oven.

[0056] Take by weighing dried D-hydroxymandelic acid · (S)-(+)-2-amino-4-phenylbutyric acid ethyl ester 9.18 ...

Embodiment 3

[0060] 12.2 grams of recovered (S)-(+)-2-amino-4-phenylbutyric acid ethyl ester hydrochloride and 8.4 grams of DL-p-hydroxymandelic acid were weighed and mixed, and other conditions were the same as in Example 1. Finally, 3.75 grams of D-p-hydroxymandelic acid was obtained, with a theoretical yield of 93.3%. D-hydroxymandelic acid has been tested, ; Chemical purity greater than 98%.

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Abstract

The invention relates to a method for splitting DL-p-hydroxymandelic acid racemate to prepare high purity D-p-hydroxymandelic acid. The method for splitting DL-p-hydroxymandelic acid is characterized in that (S)-(+)-2-amino-4-phenylethyl butyrate hydrochloride is used as resolving agent to perform chemical splitting to DL-p-hydroxymandelic acid. The method of the invention solves the problems of too many operation steps, long reaction time, low product purity, low yield and the like in the existing method for preparing high purity D-p-hydroxymandelic acid by splitting DL-p-hydroxymandelic acid racemate.

Description

technical field [0001] The invention relates to a method for splitting DL-p-hydroxymandelic acid racemate to obtain high-purity D-p-hydroxymandelic acid. Background technique [0002] DL-p-hydroxymandelic acid is an important intermediate of medicines, pesticides and spices, especially in medicine, it is an intermediate for the preparation of the new antihypertensive drug Atenolol, and it is also an intermediate for the preparation of the new spectrum antibiotic drug Amoxicillin . However, p-hydroxymandelic acid synthesized by commonly known economical and common methods does not have chirality, but p-hydroxymandelic acid which has optical activity has special uses in the field of medicine or biomedicine. For example, D-hydroxymandelic acid can be used to synthesize L-p-hydroxyphenylglycine, and then synthesize broad-spectrum antibiotics amoxicillin and amoxicillin cephalosporin, cefoperazone, cefuroxime and cefadroxol, etc. At the same time, D-hydroxymandelic acid And its...

Claims

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Application Information

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IPC IPC(8): C07C59/52C07C51/42C07B57/00
Inventor 伊汀
Owner BAOWU CHARCOAL MATERIAL TECH CO LTD
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