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

1993-02-22

1994-05-10

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07B 5300, C07B 5500, C07D20508

Patent

active

053108990

ABSTRACT:
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.

REFERENCES:
Chem. Rev., vol. 76 (1976) Russmussor et al.
Justus Liebigs Ann. Chem., 1974, 539, by Claus, et al.
10th Coll. Chem. Comps. Index, pp. 7086CS-7088CS (1985) (Cumulative).
Sunagawa, Chem Abs 104, 207051 (1986).
J.C.S. Chem. Commun., pp. 1324-1325 (1982), by Shibasaki, et al.
Chem. Absts., vol. 101, 72522Y by Takeda (1984).
Ikagami Chem. Abst., vol. 104, 33947h (1986).
Tetrahedron Letters, No. 52, 1979, G. B. pp. 5063-5066, by D. Boucherot, et al.

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