Process for the preparation of chiral 4-aryloxyazetidinones

Details Process for the preparation of chiral 4-aryloxyazetidinones Process for the preparation of chiral 4-aryloxyazetidinones

C - Chemistry, Metallurgy

07

D

C07D 205/08 (2006.01)

Patent

CA 2061577

A process for preparing a single enantiomer of a 4-aryloxyazetidin-2-one derivative in optically pure form comprises reacting a hindered vinyl ester with chlorosulphonyl isocyanate: displacing the hindered acyloxy group with a phenolic derivative containing a protected carboxy group; deprotecting the carboxylate moiety: resolving with a chiral amine; filtering: and regenerating the desired enantiomer by acidification. A method for enriching the product obtained from the acyloxy displacement step in favour of the desired enantiomeric form, by treating with an asymmetric catalyst such as a chiral alkaloid derivative, is provided: as also is a method for racemising the unwanted antipode of the desired 4-aryloxyazetidin-2-one enantiomer. The invention further provides novel enantiomers based on the 4-aryloxyazetidin-2-one ring structure.

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