The preparation method of dl-p-thymphenyl phenylserine ester

A technology of methylsulfonyl phenylserine ethyl ester and methanol, which is applied in the field of preparation of DL-p-thymphenyl phenylserine ester, can solve the problems of long recycling period and low production capacity, so as to improve efficiency, simplify production process, reduce pollution effect

Active Publication Date: 2022-05-03
ZHEJIANG KANGMU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • The preparation method of dl-p-thymphenyl phenylserine ester
  • The preparation method of dl-p-thymphenyl phenylserine ester
  • The preparation method of dl-p-thymphenyl phenylserine ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Take L- p-methyl sulfonylphenylserine ethyl ester 28.7g (0.1mol), disperse it into 170g of water, control the temperature at 15 °C (temperature difference ± 2 °C), insulation stirring for 30 minutes, add a concentration of 30wt% sodium hydroxide solution 3.9g, insulation reaction for 8 hours, after which the pH value was adjusted to 7.0, and then filtered to obtain the product D- p-methyl sulfonyl phenylserine ethyl ester and L- p-methylsulfonylphenylserine ethyl ester for a total of 18.52g. as Figure 1 As shown, the characteristic peak at 11.491min is the characteristic peak of D- p-methylsulfonyl phenylserine ethyl ester, and the characteristic peak at 14.736min is L- p-methylsulfonylphenylserine ethyl characteristic peak, and the ratio of D- p-methylsulfonylphenylserine ethyl ester and L- p-methylsulfonylphenylserine ethyl ester is 46.6%:53.1%, that is, 1:1.1, close to 1:1.

Embodiment 2

[0040] Take L- p-methyl sulfonylphenylserine ethyl ester 28.7 g (0.1 mol), dispersed into 170 g ethanol, the temperature was controlled at 15 °C (temperature difference ± 2 °C), after heat preservation stirring for 30 minutes, the concentration of 10% sodium hydroxide solution 11.5 g, the insulation reaction for 10 hours, and then the pH value was adjusted to 7.0, filtered to give the product D- p-methyl sulfone phenyl serine ethyl ester and L- p-methyl sulfone phenyl serine ethyl ester a total of 15.32 g. as Figure 2 As shown, at 11.369min the characteristic peak is the characteristic peak of D- p-methylsulfonylphenylserine ethyl ester, at 14.541min the characteristic peak is L- p-methylsulfonylphenylserine ethyl ester characteristic peak, the ratio of D- p-methyl sulfonylphenylserine ethyl ester and L- p-methylsulfonylphenylserine ethyl ester is 47.6%: 52.2%, that is, 1: 1.1, close to 1: 1.

Embodiment 3

[0042] Take L- p-methyl sulfonylphenylserine ethyl ester 28.7g (0.1mol), dispersed into 170g of methanol, the temperature was controlled at 15 °C (temperature difference ±2 °C), stirred for 30 minutes, with 10% sodium hydroxide solution 11.5g, insulation reaction for 10 hours, and then the pH value was adjusted to 7.0, filtered to give the product D- p-methylsulfonyl phenylserine ethyl ester and L- p-methyl sulfonylphenylserine ethyl ester a total of 13.32g. as Figure 3As shown, at 10.798min the characteristic peak is D- p-methylsulfonylphenylserine ethyl characteristic peak, at 14.622min the characteristic peak is L- p-methylsulfonylphenylserine ethyl characteristic peak, the ratio of D- p-methylsulfonylphenylserine ethyl ester and L- p-methylsulfonylphenylserine ethyl ester is 49.2%: 49.6%, that is, 1: 1.0, 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-thiamphenicyl phenylserine ester. DL-p-thiamphenicol phenylserine ester is prepared by reacting L-p-thiamphenicol phenylserine ester or its salt, specifically comprising two Method, one, L-p-thiamphenyl phenylserine ester or its salt is directly produced after racemization DL-p-thiamphenicol phenylserine ester, the second, L-p-thiamphenicyl phenylserine ester or its salt After lye racemization and saponification, DL-p-thiamphenyl phenylserine or salt is obtained, and then copper reagent is used to obtain D-p-thiamphenyl phenylserine copper, and finally esterified to obtain DL-p-thiamphenyl phenylserine Serine ester. The invention simplifies the existing production process of DL-p-thymphenylphenylserine ester, greatly improves the recovery efficiency; solves the complex recovery process of racemic copper salt in the existing process, reduces pollution, and is more conducive to industrial production.

Description

Technical field [0001] The present invention relates to the field of pharmaceutical synthesis technology, in particular to a DL- method for preparing p-methyl sulfonylphenylserine ester. Background [0002] Florfenicol, also known as flumethamycin, fluorosulfone nico, is a class of chemically synthesized and specifically used in the animal health market broad-spectrum antibacterial drugs, its structure is similar to thiamphenicol, there are two chiral centers, four corresponding isomers, its bactericidal capacity is 10 times that of thiamphenicol, and safe and efficient, especially the aplastic anemia of chloramphenicol antibiotics. The global demand for thiamphenicol and florfenicol drugs exceeds 2,000 tons and the growth trend is clear. Because D-p-methyl sulfonylphenylserine ethyl ester is the main intermediate of thiamphenicol, its market demand has reached more than 2500 tons, and at a rate of more than 15% per year continues to increase, the domestic and foreign market dem...

Claims

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Application Information

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Patent Type & Authority Patents(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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