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Synthesis method of 2-hydroxyl-3-(3,4-dimethoxy phenyl)propionic acid

A technology of dimethoxyphenyl and synthetic methods, applied in the field of synthesis of 2-hydroxy-3-propionic acid, can solve the difficult to meet the needs of impurity research, low purity of L-350 impurity A, difficult to handle waste, etc. problems, to achieve the effects of low toxicity, easy handling, and environmental protection

Inactive Publication Date: 2018-06-01
SHANDONG XINHUA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the above synthetic route, zinc-mercury hydrochloric acid is used as a catalyst. After the reaction, a mixture of zinc chloride and mercury chloride is produced, which is difficult to separate, and the prepared L-350 impurity A has low purity, which is difficult to meet the needs of impurity research, and, Wastes that are not easy to handle will be generated during the reaction process, which is not conducive to environmental protection

Method used

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  • Synthesis method of 2-hydroxyl-3-(3,4-dimethoxy phenyl)propionic acid
  • Synthesis method of 2-hydroxyl-3-(3,4-dimethoxy phenyl)propionic acid
  • Synthesis method of 2-hydroxyl-3-(3,4-dimethoxy phenyl)propionic acid

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Embodiment 1

[0029] Add 10g (0.04mol) of B to a 1L autoclave, 26.6g (0.2mol) of 30% liquid caustic soda, and 85mL of water, keep the temperature at 127.5±2.5°C, and react at a pressure of 0.3±0.1MPa for 5 hours, then concentrate under reduced pressure. Adjust the pH to 5 with hydrochloric acid. Cool down to 5°C, filter and wash with water to obtain 5.6 g of yellow crystals. The yield is 61.9%, the melting point is 103-105°C, and the purity is 99.4%.

Embodiment 2

[0031] Add 10g (0.04mol) of B to a 1L autoclave, 21.6g (0.12mol) of 30% sodium methoxide, and 80mL of methanol, keep the temperature at 65±5°C, and react at a pressure of 0.9±0.1MPa for 8 hours, then concentrate under reduced pressure. Adjust the pH to 5.5 with hydrochloric acid. Cool down to 6°C, filter and wash with water to obtain 7.2 g of yellow crystals. The yield is 79.5%, the melting point is 103-105°C, and the purity is 99.3%.

Embodiment 3

[0033] Add 10g (0.04mol) of B to a 1L autoclave, 60.4g (0.16mol) of 18% sodium ethoxide, and 50mL of ethanol, keep the temperature at 75±5°C, and react at a pressure of 0.7±0.1MPa for 12 hours, then concentrate under reduced pressure. Adjust the pH to 5.5 with hydrochloric acid. Cool down to 8°C, filter and wash with water to obtain 5.2 g of yellow crystals. Yield 57.5%. The melting point is 103-105°C, and the purity is 99.7%.

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Abstract

The invention belongs to the field of medicine preparation and specifically relates to a synthesis method of 2-hydroxyl-3-(3,4-dimethoxy phenyl)propionic acid. The synthesis method of 2-hydroxyl-3-(3,4-dimethoxy phenyl)propionic acid comprises the following steps: with veratral hydantoin as a raw material and alkali as a catalyst, closing and pressurizing for reacting; after the reaction is completed, performing vacuum concentration, neutralizing, cooling, filtering and washing to obtain 2-hydroxyl-3-(3,4-dimethoxy phenyl)propionic acid. The synthesis method provided by the invention has the advantages of easily available raw material, low toxicity, few wastes, easiness in treatment, promotion of environmental protection, high-purity target product and satisfaction of the needs for impurity research.

Description

technical field [0001] The invention belongs to the field of medicine preparation, and in particular relates to a synthesis method of 2-hydroxy-3-(3,4-dimethoxyphenyl)propionic acid. Background technique [0002] 2-Hydroxy-3-(3,4-dimethoxyphenyl)propionic acid (referred to as L-350 impurity A) is a by-product of the synthesis of N-acetyl-DL-veratrylglycine (referred to as L-350) , L-350 is an important intermediate of the anti-Parkinson's disease drug dopa, and the research on its impurities is directly related to the quality and process stability of the product, so as to avoid being generated as a by-product when preparing L-350. [0003] [0004] Synthesis: 1992.August, 793, report: use veratraldehyde and acetylglycine as raw materials, react at 90-120°C in the presence of acetic anhydride and sodium acetate, then hydrolyze with 3N hydrochloric acid, and reduce with Zn / Hg to obtain L-350 impurity A . Its synthetic route is: [0005] [0006] In the above synthetic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/02C07C59/64
CPCC07C51/02C07C51/06C07D233/96C07C59/64
Inventor 黄爱军李兴泰潘西海赵丽于磊张岱宋丽华
Owner SHANDONG XINHUA PHARMA CO LTD
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