Bicyclic beta-lactams and process therefor

Details Bicyclic beta-lactams and process therefor Bicyclic beta-lactams and process therefor

1995-06-19

1998-05-12

Mullis, Jeffrey

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20700

Patent

active

057506817

ABSTRACT:
Bicyclic .beta.-lactams comprising a 5- or 6-membered lactone or lactam ring are obtained in a process comprising a base induced intramolecular cyclization of a 4-substututed .beta.-lactam having a leaving group in the 1-position. An intramolecular nucleophile transfer reaction is proposed as the operative mechanism and the bicyclic .beta.-lactams are obtained in the required stereochemical form for biological activity. The compounds provided are useful intermediates for the preparation of antibiotics and .beta.-lactamase inhibitors.

REFERENCES:
patent: 4885362 (1989-12-01), Morin, Jr. et al.
patent: 4892942 (1990-01-01), Munro
patent: 5250676 (1993-10-01), Gasparski et al.
Guzzo, Teng, Miller, Tetrahedron vol. 50, pp. 8275-8292, Jul. 1994.
M. Teng M.J. Miller, J. Am. Chem. Soc. No. 2, pp. 548-554, Jan. 1993.

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