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Preparation method of methyl D-4-hydroxy-phenylglycinate and hydrochloride thereof

A technology of p-hydroxyphenylglycine methyl ester and p-hydroxyphenylglycine, which is applied in the field of synthesis of pharmaceutical intermediate D-p-hydroxyphenylglycine methyl ester and its hydrochloride, which can solve the problems of high production cost, high environmental protection pressure and cumbersome operation and other problems, to achieve the effect of less environmental pollution, convenient post-processing, and simple operation process

Inactive Publication Date: 2014-03-19
河北爱弗特精细化工有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, there are defects such as high production cost, low yield, cumbersome operation, and high environmental protection pressure in the prior art

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Mix 8.35g (0.05mol) D-p-hydroxyphenylglycine with 50mL methanol, stir well; control the reaction temperature at 0-5°C, slowly add 10.9g (0.1mol) trimethylchlorosilane dropwise; after the dropwise addition, The reaction was carried out at room temperature of 25°C, and the end point of the reaction was detected by TLC. After the reaction, the reaction solution was concentrated to obtain a white solid, which was dissolved in 40 mL of water, neutralized with 10% aqueous sodium hydroxide solution to pH=9, filtered, and dried to obtain 7.9 g of D-p-hydroxyphenylglycine methyl ester, with a yield of 87.5%. Purity (HPLC) 98.8%.

Embodiment 2

[0019] Mix 8.35g (0.05mol) of D-p-hydroxyphenylglycine with 58mL of methanol and stir evenly; slowly add 13.6g (0.125mol) of trimethylchlorosilane dropwise at room temperature; after the addition is completed, the temperature is raised to 50°C, and the reaction endpoint is monitored by TLC . After the reaction was completed, the temperature was lowered and cooled, and the reaction solution was concentrated under reduced pressure to obtain a white solid, dissolved in 40 mL of water, neutralized with aqueous sodium carbonate to pH=8.5, filtered, and dried to obtain 8.0 g of p-hydroxyphenylglycine methyl ester, with a yield of 88.5 %, HPLC purity is 98.1%.

Embodiment 3

[0021] Mix 8.35g (0.05mol) D-p-hydroxyphenylglycine with 42mL methanol, stir well; control the reaction temperature at 0~10°C, slowly add 10.9g (0.1mol) trimethylchlorosilane dropwise; heat up after the dropwise addition To 60°C, TLC detects the end point of the reaction. After the reaction was completed, the temperature was lowered and cooled, the reaction solution was concentrated under reduced pressure to obtain a white solid, dissolved in 40 mL of water, neutralized with 10% sodium carbonate solution to pH = 8.5, filtered, and dried to obtain p-D-hydroxyphenylglycine methyl ester 8.45 g, yield 93.4%, HPLC purity is 97.8%.

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Abstract

The invention discloses a preparation method of D-4-hydroxy-phenylglycinate and hydrochloride thereof. D-4-hydroxyphenylglycine is used as an initial raw material. The methyl D-4-hydroxy-phenylglycinate or the hydrochloride thereof is prepared by reacting the D-4-hydroxyphenylglycine with methanol or a methanol solution of hydrogen chloride under the existence of trimethylchlorosilane and by post-treatment. The preparation method has characteristics of easily available raw materials, simple operation, high yield, high product purity and little environment pollution, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the synthesis of a pharmaceutical intermediate D-p-hydroxyphenylglycine methyl ester and its hydrochloride, which belongs to the field of medicine and chemical industry. Background technique [0002] D-p-Hydroxyphenylglycine methyl ester is the side chain of enzymatic synthesis of amoxicillin and cefadroxil. The early production method of amoxicillin and cefadroxil was: D-p-Hydroxyphenylglycine Dunk’s salt and pivaloyl chloride in the presence of acid-binding agents to form mixed anhydrides, and then mixed with penicillin nucleus or The cephalosporin nucleus is condensed with an organic alkali solution, and the product is obtained through hydrolysis, crystallization and drying. The production method has serious environmental pollution, harsh conditions, needs organic solvents, and complicated process. In recent years, the technology of enzymatic production of antibiotics has been widely used abroad, and domestic manufacturer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C227/18
Inventor 付德才郑美玲谷明明张伟石少龙单国申张中文
Owner 河北爱弗特精细化工有限责任公司
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