Merck Sharp + Dohme Corp.

Merck Sharpe & Dohme Corp.

Brian Cchristopher Bishop

Guy R Humphrey

Ian Frank Cottrell

Michael Stewart Ashwood

Mark Cameron

David Hands

Peter G Houghton

The present invention relates to a process for the preparation of azaindole derivatives of the formula ##STR1## wherein Q is hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.1-6 alkoxy, hydroxy, aryl or arylC.sub.1-4 alkyl;

Chemical synthesis of azaindoles

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.

Process for the preparation of chiral 4-aryloxyazetidinones

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Bishops Stortford, United Kingdom

Brian Cchristopher Bishop