Industrial production process of 3R, 4R-3-[(1R)-tert-butyl dimethyl siloxane ethyl]-4-acetoxyl-2-azetinone

Abstract

The present invention provides 4-AA preparing process with (2S,3S)-2-benzoylaminomethyl-3- hydroxy butanoic ester, which is prepared with 2- benzoylaminomethyl-3-carbonyl butanoic ester, as material. The 4-AA preparing process has low cost, high yield, reaction condition suitable for industrial production and other advantages.

Description

technical field [0001] The present invention relates to 3R shown in formula (I), 4R-3-[(1R)-tert-butyldimethylsiloxyethyl]-4-acetoxy-2-azetidinone (abbreviated as 4 -Asymmetric synthesis of AA). The 4-AA prepared by the invention is a key intermediate for the industrial production of carbapenems and penems. [0002] [0003] Formula 1. Background technique [0004] Azetidinone compound 3R, 4R-3-[(1R)-tert-butyldimethylsiloxyethyl]-4-acetoxy-2-azetidinone (formula (I), referred to as 4-AA) is a key intermediate in the synthesis of new high-efficiency antibiotics carbapenems and penems, such as for the synthesis of carbapenem antibiotics imipenem, meropenem, faropenem and panipene Nan et al. [0005] 4-AA has 3 chiral centers, so there are 8 stereoisomers, which is very difficult to synthesize. There have been literature reviews on the synthesis process of 4-AA, but most of the processes have disadvantages such as long synthetic route, lo...

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Problems solved by technology

[0005] 4-AA has 3 chiral centers, so there are 8 stereoisomers, which is very difficult to synthesize

There has been a review of the literature on the synthesis process of 4-AA, but most of the processes have the disadvantages of long synthetic route, low total yield, cumbersome operation, and high cost, thus limiting the industrial production of formula 4-AA

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