Rhodium catalyzed cyclization process for bicyclic .beta.-lactam

Details Rhodium catalyzed cyclization process for bicyclic .beta.-lactam Rhodium catalyzed cyclization process for bicyclic .beta.-lactam

1990-06-06

1991-09-24

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540302, 540355, C07D205085, C07D20508, C07D48704

Patent

active

050515020

ABSTRACT:
1-Carbapenam-2-one-3-carboxylic acid and 1-carba-3-hydroxy-3-cephem-4-carboxylic acid and esters thereof are provided by a process comprising a rhodium C.sub.2 -C.sub.10 carboxylate catalyzed cyclization of an ester of a 4-(1-alkoxy- or 1-substituted alkxoy)-2-oxo-4-azetidinyl)-.alpha.-diazo-.beta.-ketobutyric acid and an ester of a 5-(1-alkoxy- or 1-substituted alkoxy-2-oxo-4-azetidinyl)-.alpha.-diazo-.beta.-ketovaleric acid respectively. The process is carried out in an inert organic solvent at a temperature between about 15.degree. C. and about 85.degree.0 C. The 1-carba bicyclic .beta.-lactams are intermediates for preparing antibiotics.

REFERENCES:
Padwa, J. Org. Chem. 55, 405 (1990).

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