A method for preparing chiral (2s, 3r)-p-thymphenylphenylserine ethyl ester

Abstract

The invention provides a method for preparing (2S, 3R)-p-methyl sulfone phenyl ethyl serinate from the cheap and easily available methylsulfonyl benzaldehyde and L-threonine under the action of transaldolase. The amino acid intermediate then undergoes ethyl esterification to obtain a target product (2S, 3R)-p-methyl sulfone phenyl ethyl serinate.

Description

technical field [0001] The invention belongs to the technical fields of biological pharmacy and biochemical industry, and in particular relates to a preparation method of chiral (2S, 3R)-p-thymphenylphenylserine ethyl ester. Background technique [0002] Florfenicol is a broad-spectrum antibacterial drug, mainly used for bacterial diseases of cattle, pigs, chickens, ducks, fish and other animals. Thiamphenicol is a drug mainly used for human treatment of respiratory, urinary, hepatobiliary, typhoid and other intestinal surgery, obstetrics and gynecology and ENT infections, especially for moderate and mild infections. (2S,3R)-P-thymphenylphenylserine ethyl ester is a key intermediate in the synthesis of these drugs. Therefore, exploring a mild, efficient and economical method to prepare (2S,3R)-p-thymphenylphenylserine ethyl ester has attracted the attention of chemical and biological workers. [0003] (2S,3R)-P-thymphenylphenylserine ethyl ester, its structural formula is ...

AI Technical Summary

Problems solved by technology

[0008] 1. This route requires chiral resolution, and the theoretical yield of the resolution is only 50%, which leads to the yield of the whole route being below 35%. In addition, the steps of resolution are very cumbersome, which brings a great deal of burden to industrial production. the inconvenience

[0009] 2. A large amount of copper salt needs to be used in the condensation process of this route, and the whole process produces a large amount of waste water with metal copper ions; in addition, the splitting process of the racemate also produces a large amount of waste water and solid waste. This method is harmful to the environment. very dangerous

[0010] 3. In this route, in order to remove the residual copper ions in the product, it is necessary to use foul-smelling hydrogen sulfide gas, and the treatment of waste gas is also a major difficulty in this process

[0015] At present, this method still has defects such as low conversion rate, large amount of glycine, poor stereoselectivity, and difficult separation and purification of products, and it does not yet have the conditions for industrialization.

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