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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  • Abstract
  • Description
  • Claims
  • Application Information

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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 o

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

Example Embodiment

[0049] Example 1

[0050] Take 8.4 grams (0.05mol) of DL-p-hydroxymandelic acid, 12.18 grams (0.05mol) of ethyl (S)-(+)-2-amino-4-phenylbutyrate hydrochloride, and put it into 120ml 30% In the ethanol aqueous solution, turn on the 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 30 minutes, a white precipitate will appear, slowly reduce the temperature to 10°C to allow the formation of D- The double salt of p-hydroxymandelic acid was fully analyzed. Filtrate under reduced pressure to obtain filtrate A and 9.07 g of white crystals. The yield is 97% of the theoretical yield. The white crystals are D-p-hydroxymandelic acid double salt (D-p-hydroxymandelic acid·(S)-(+) -2-amino-4-phenylbutyrate), washed with a small amount of ethanol, and dried in a vacuum drying oven.

[0051] Weigh 9.07 grams of dried D-p-hydroxymandelic acid·(S)-(+)-2-amino-4-phenylbutyric acid e...

Example Embodiment

[0054] Example 2

[0055] Take (S)-(+)-2-amino-4-phenylbutyric acid ethyl ester hydrochloride 12.18g (0.05mol), put it into 120ml ethanol aqueous solution with a concentration of 50% by mass, turn on the stirring, N 2 Protect, heat up to 55°C, and then slowly add 2 grams (0.05 mol) of sodium hydroxide to form a transparent reaction solution. Subsequently, 8.4 grams (0.05 mol) of DL-p-hydroxymandelic acid was added, and after the stirring reaction was continued for 80 minutes, white precipitates were generated. The temperature was slowly lowered to 10° C., and the formed D-p-hydroxymandelic acid double salt was fully analyzed. 9.18 g 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 is washed with a small amount of ethanol and then dried in a vacuum drying oven.

[0056] Weigh 9.18 g of dried D-p-hydroxymandelic acid·(S)...

Example Embodiment

[0059] Example 3

[0060] Weigh 12.2 g of the recovered (S)-(+)-2-amino-4-phenylbutyric acid ethyl ester hydrochloride and 8.4 g of DL-p-hydroxymandelic acid, and mix the other conditions as in Example 1. Finally, 3.75 g of D-p-hydroxymandelic acid was obtained with a theoretical yield of 93.3%. D-p-hydroxymandelic acid has been tested, ; The chemical purity is 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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