Process for preparing 1'-hydroxy-2'-substituted cyclohexyl azetidin-2-one compounds

By using Lewis acid catalyst under ultrasonic radiation or microwave radiation, the yield of 1'-hydroxy-2'-substituted cyclohexyl azetidin-2-one is improved, and the low yield in the existing technology is solved. problem, providing an efficient intermediate preparation method for carbapenem synthesis.

CN101268086AInactive Publication Date: 2008-09-17LEK PHARMA D D
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Patent Information

Application Number
CN200680034105.2
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2005-09-21
Filing Date
2006-09-19
Publication Date
2008-09-17
Estimated Expiration
Not applicable · inactive patent

AI Technical Summary

Technical Problem

The existing technology has a low yield in the preparation of 1'-hydroxy-2'-substituted cyclohexyl azetidin-2-one, especially the lack of efficient intermediate preparation methods in the synthesis of carbapenems.

Method used

Use (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy]ethyl]-4-[(1'R,2'S,3'R)-1 ',2'-epoxycyclohexane-3'- The epoxide ring-opening reaction of azetidin-2-one is carried out by ultrasonic radiation or microwave radiation in a suitable solvent, and a Lewis acid catalyst such as trifluoromethanesulfonate is used for catalysis to increase the reaction yield. .

Benefits of technology

Significantly improves the yield of 1’-hydroxy-2’-substituted cyclohexyl azetidin-2-one, provides important intermediates in carbapenem synthesis, and improves synthesis efficiency and yield.

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Abstract

A novel process for the preparation of 1'-hydroxy-2'-substituted cyclohexyl azetidin-2- one compound of formula 2, which is important intermediate in the synthesis of trinems, is described by epoxide ring opening of (3S,4R)-3-[(1R)-1-(tert- butyldimethylsilyloxy)ethyl]-4-[(1'R,2'S,3'R)-1',2'-epoxycyclohexan-3'-yl]azetidin-2-one of formula 1 with the nucleophile compound of formula RYH, where nucleophile may act as solvent itself if the nucleophile is in the liquid form, in a suitable solvent and in the presence of a suitable catalyst from the group of salt of trifluoromethane sulfonic acid, preferably ytterbium (III) trifluoromethanesulfonate, stannous (II) trifluoromethanesulfonate or dysprosium (III) trifluoromethanesulfonate, under a) ultrasonic irradiation or b) under microwave irradiation of the reaction mixture following by isolation and purification of the desired compound.; A variant of the novel process describes ring epoxide opening of the starting compound of formula 1 with the compound of formula NH4X in a suitable solvent under a) microwave irradiation or b) without microwave irradiation to obtain the desired compound of formula 2. Instead of compound of formula 1 a compound of formula 6 may be used as starting compound where any other suitable hydroxy protecting group known in the art may be used in the formula of the starting compound.
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