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Preparation method of DL-p-methylsulfonylphenylserine ester

A technology of methylsulfonyl phenylserine ester and methylsulfonyl phenylserine, which is applied in the field of drug synthesis, can solve the problems of low production capacity, long recovery cycle and the like, and achieves the effects of simplifying production process, improving efficiency and reducing pollution

Active Publication Date: 2020-06-19
ZHEJIANG KANGMU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With this intermediate racemate, there are problems of long cycle and low production capacity in the recycling of materials

Method used

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  • Preparation method of DL-p-methylsulfonylphenylserine ester
  • Preparation method of DL-p-methylsulfonylphenylserine ester
  • Preparation method of DL-p-methylsulfonylphenylserine ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Take 28.7g (0.1mol) of L-p-thymphenylphenylserine ethyl ester, disperse it into 170g of water, control the temperature at 15°C (temperature difference ±2°C), keep stirring for 30 minutes, then add hydrogen with a concentration of 30wt% Sodium oxide solution 3.9g, heat preservation reaction for 8 hours, then adjust the pH value to 7.0, and then filter to obtain a total of 18.52g of the product D-p-thiamphenyl phenylserine ethyl ester and L-p-thiamphenyl phenylserine ethyl ester. Such as figure 1 As shown, the characteristic peak at 11.491min is the characteristic peak of D-p-thymphenyl phenylserine ethyl ester, and the characteristic peak at 14.736min is the characteristic peak of L-p-thymphenyl phenylserine ethyl ester. In the product, D-p-methyl The ratio of sulfonyl phenylserine ethyl ester to L-p-thiamphenyl phenylserine ethyl ester is 46.6%:53.1%, which is 1:1.1, which is close to 1:1.

Embodiment 2

[0039] Take 28.7g (0.1mol) of L-p-thymphenylphenylserine ethyl ester, disperse it into 170g of ethanol, control the temperature at 15°C (temperature difference ±2°C), keep stirring for 30 minutes, and then add a concentration of 10% hydroxide 11.5 g of sodium solution was incubated for 10 hours, then the pH value was adjusted to 7.0, and 15.32 g of the product D-p-thiamphenylphenylserine ethyl ester and L-p-thiamphenyl phenylserine ethyl ester were obtained by filtration. Such as figure 2 As shown, the characteristic peak at 11.369min is the characteristic peak of D-p-thymphenyl phenylserine ethyl ester, and the characteristic peak at 14.541min is the characteristic peak of L-p-thymphenyl phenylserine ethyl ester. In the product, D-p-methyl The ratio of sulfonyl phenylserine ethyl ester to L-p-thiamphenyl phenylserine ethyl ester is 47.6%:52.2%, which is 1:1.1, which is close to 1:1.

Embodiment 3

[0041] Take 28.7g (0.1mol) of L-p-thymphenylphenylserine ethyl ester, disperse it in 170g of methanol, control the temperature at 15°C (temperature difference ±2°C), keep stirring for 30 minutes, then use 10% sodium hydroxide solution 11.5 g, heat preservation reaction for 10 hours, then adjust the pH value to 7.0, and filter to obtain a total of 13.32 g of the product D-p-thiamphenyl phenylserine ethyl ester and L-p-thiamphenyl phenyl serine ethyl ester. Such as image 3 As shown, the characteristic peak at 10.798min is the characteristic peak of D-p-thymphenyl phenylserine ethyl ester, and the characteristic peak at 14.622min is the characteristic peak of L-p-thymphenyl phenylserine ethyl ester. In the product, D-p-methyl The ratio of sulfonyl phenylserine ethyl ester to L-p-thiamphenyl phenylserine ethyl ester is 49.2%:49.6%, which is 1:1.0, which is close to 1:1.

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Abstract

The invention belongs to the technical field of medicine synthesis. The invention discloses a preparation method of DL-p-methylsulfonylphenylserine ester. DL-p-methylsulfonylphenylserine ester is prepared from L-p-methylsulfonylphenylserine ester or a salt thereof through reaction. Specifically, two methods are included. In a first method, L-p-methylsulfonylphenylserine ester or salt thereof is directly racemized to obtain DL-p-methylsulfonylphenylserine ester. In a second method, L-p-methylsulfonylphenylserine ester or a salt thereof is subjected to alkali liquor racemization and saponification to obtain DL-p-methylsulfonylphenylserine or a salt thereof, then a copper reagent is adopted to prepare D-p-methylsulfonylphenylserine copper, and finally esterification is performed to obtain theDL-p-methylsulfonylphenylserine ester. According to the method disclosed by the invention, an existing DL-p-methylsulfonylphenylserine ester production process is simplified, and the recovery efficiency is greatly improved; and the method solves the problem of complex racemization copper salt recovery process in the prior art, reduces pollution, and is more beneficial to industrial production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of DL-p-thymphenylphenylserine ester. Background technique [0002] Florfenicol, also known as florfenicol and florfenicol, is a broad-spectrum antibacterial drug that is chemically synthesized and specially used in the animal health market. Its structure is similar to that of thiamphenicol, and it has two chiral The center, four enantiomers, its bactericidal ability is 10 times that of thiamphenicol, and it is safe and efficient, especially for aplastic anemia caused by chloramphenicol antibiotics. The global demand for thiamphenicol and florfenicol exceeds 2,000 tons, and the growth trend is clear. Because D-thiamphenicol phenylserine ethyl ester is the main intermediate of thiamphenicol, its market demand has reached more than 2,500 tons, and it continues to increase at a rate of more than 15% per year. The domestic and foreign market demand is ext...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/48C07B55/00
CPCC07C315/04C07B55/00C07C317/48
Inventor 袁庆王法平张立光王小祥杜长路
Owner ZHEJIANG KANGMU PHARMA
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