The preparation method of d-phenylglycine methyl ester hydrochloride/d-dihydrophenylglycine methyl ester hydrochloride

A technology of dihydrophenylglycine methyl ester and dihydrophenylglycine, applied in the field of preparation of D-phenylglycine methyl ester hydrochloride/D-dihydrophenylglycine methyl ester hydrochloride, can solve product quality problems Low, affecting production and other issues, to achieve high purity, conducive to industrial production, and increase profits

Active Publication Date: 2022-03-01
NORTH CHINA PHARMA COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of preparation method of D-phenylglycine methyl ester hydrochloride / D-dihydrophenylglycine methyl ester hydrochloride, to solve the low product quality when existing method mother liquor applies mechanically, influence follow-up production question

Method used

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  • The preparation method of d-phenylglycine methyl ester hydrochloride/d-dihydrophenylglycine methyl ester hydrochloride
  • The preparation method of d-phenylglycine methyl ester hydrochloride/d-dihydrophenylglycine methyl ester hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0028] in 2M 3 In the reaction tank, add 1200L of methanol, and add 400Kg of D-phenylglycine while stirring. After stirring evenly, add 460Kg of thionyl chloride, and control the temperature below 50°C. 4h, the reaction ends. Then carry out vacuum distillation, and the vacuum degree in the reactor is maintained at 0.03MPa. After the mass content of methanol in the solution in the reaction tank reaches 15%, stop the vacuum distillation, cool down and crystallize, drop to 0°C, stir for 30-60min, then centrifuge, and vacuum-dry at 50°C for 8h to obtain D-phenylglycine methyl ester salt Salt 480Kg.

[0029] The volume of the mother liquor was 250L, and then vacuum concentrated to 62.5L, cooled to 0°C, and then centrifuged to obtain a yellow recovered product; the recovered product was rinsed with 4Kg of methyl acetate, and vacuum-dried at 50-60°C to obtain a white recovered product of 26.0Kg ( The content of D-phenylglycine is 31.0%); the recovered product is applied mechanical...

Embodiment 2

[0031] in 2M 3 Add 1223.4L of methanol to the reaction tank, add 400Kg of D-phenylglycine and 26Kg of recovered product (containing 31.0% phenylglycine) under stirring, after stirring evenly, add 469Kg of thionyl chloride, control the temperature below 50°C, and complete the dropwise addition Afterwards, the temperature in the reactor was maintained at 59° C., and the reaction was completed by reflux for 4 hours. Then carry out vacuum distillation, and the vacuum degree in the reactor is maintained at 0.03MPa. After the mass content of methanol in the solution in the reaction tank reaches 15%, stop the vacuum distillation, cool down and crystallize, drop to 0°C, stir for 30-60min, then centrifuge, and vacuum-dry at 50°C for 8h to obtain D-phenylglycine methyl ester salt Salt 508Kg (mol yield: 95.49%), purity 99.6%, color grade and turbidity both 1#, light transmission 98.4%, see Table 1 for details.

[0032] The volume of the mother liquor is 250L, then vacuum concentrated t...

Embodiment 3

[0034] in 2M 3 Add 1223.4L of methanol to the reaction tank, add 400Kg of D-phenylglycine and 26Kg of recovered product (containing 31.4% of phenylglycine) under stirring, after stirring evenly, add 469Kg of thionyl chloride, control the temperature below 50°C, and complete the dropwise addition Afterwards, the temperature in the reactor was maintained at 60° C., refluxed for 4 hours, and the reaction was completed. Then carry out vacuum distillation, and the vacuum degree in the reactor is maintained at 0.03MPa. After the mass content of methanol in the solution in the reaction tank reaches 16%, stop the vacuum distillation, cool down and crystallize, drop to 0°C, stir for 30-60min, then centrifuge, and vacuum dry at 50°C for 8h to obtain D-phenylglycine methyl ester salt Salt 509Kg (mol yield: 95.68%), purity 99.7%, color grade and turbidity both 1#, light transmission 98.5%, see Table 1 for details.

[0035] The volume of the mother liquor is 250L, then concentrated in va...

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Abstract

The invention provides a preparation method of D-phenylglycine methyl ester hydrochloride / D-dihydrophenylglycine methyl ester hydrochloride, comprising the following steps: (a) mixing D-phenylglycine or D-dihydrobenzene Glycine and methanol were added to the reaction tank at a ratio of 1g: 3~5mL, and after stirring evenly, slowly added thionyl chloride; (b) reflux reaction after the addition of thionyl chloride; (c) vacuum distillation, Then cool down and crystallize, centrifuge and dry to obtain a white product; (d) recover the reaction mother liquor, concentrate the mother liquor in a vacuum, cool down and crystallize, and centrifuge to obtain a yellow recovered product; (e) wash the yellow recovered product with an organic reagent, and dry it in a vacuum to obtain White recycled product; (f) Apply the white recycled product to the reaction tank, and then follow steps (a)~(c) to prepare the next batch of products. The invention proposes a new way of applying the mother liquor, so that the product quality is more stable, the purity is high, and the color grade and turbidity are excellent.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a preparation method of D-phenylglycine methyl ester hydrochloride / D-dihydrophenylglycine methyl ester hydrochloride. Background technique [0002] D-phenylglycine methyl ester hydrochloride, D-dihydrophenylglycine methyl ester hydrochloride is white powder or crystal, D-phenylglycine methyl ester hydrochloride is the side of enzymatic ampicillin, cephalexin, cefaclor Chain, D-dihydrophenylglycine methyl ester hydrochloride is the side chain of enzymatic cephradine. [0003] The synthesis method of D-phenylglycine methyl ester hydrochloride mentioned in "Synthesis of Cefaclor Active Side Chain Phenylglycine Methyl Ester Hydrochloride" published by Zheng Guixian (Zhejiang Angli Pharmaceutical Co., Ltd.) in 2014 is to use dichloro Thionization method, which is to slowly add thionyl chloride to methanol solution below 35°C to generate methyl sulfo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/18C07C229/36C07C229/32
CPCC07C227/18C07C229/36C07B2200/07C07C2601/16C07C229/32
Inventor 张军立孙华刘倩张致一赵庆年赵华李珠徐颖
Owner NORTH CHINA PHARMA COMPANY
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