Monocyclic beta-lactams and process for the preparation thereof

Details Monocyclic beta-lactams and process for the preparation thereof Monocyclic beta-lactams and process for the preparation thereof

1986-07-25

1991-02-12

Berch, Mark L.

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

Organic compounds

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

C07D205085, C07D20508, C07D20509, C07D41712

Patent

active

049925440

ABSTRACT:
Monocyclic .beta.-lactam compounds represented by the formula ##STR1## wherein R.sub.1 is H, NH.sub.2, acylamino, C.sub.1 -C.sub.4 alkyl, etc.; R.sub.2 is e.g. C.sub.1 -C.sub.4 alkyl, hydroxyalkyl, aminoalkyl, carboxy, esterified carboxy, esterified carboxyalkyl, or carboxyalkyl; and R.sub.3 is hydrogen, benzyl, substituted benzyl, pivaloyl, --SO.sub.3 M, or --P(C.dbd.O)(OM')2; are obtained by the cyclization of an O-substituted hydroxamate of a .beta.-substituted alkylcarboxylic acid. For example, .alpha.-ethylmalic acid monobenzyl ester is reacted with O-benzylhydroxylamine to form the O-benzylhydroxamate of the free carboxy group, and the hydroxamate is cyclized with diethyl diazodicarboxylate and triphenylphosphine to form the .beta.-lactam of the above formula wherein R.sub.1 is ethyl, R.sub.2 is benzyloxycarbonyl and R.sub.3 is benzyl. The .beta.-lactam compounds are useful intermediates for preparing .beta.-lactamase inhibitors and monocyclic .beta.-lactam antibiotics and, when R.sub.3 is --SO.sub.3 M or --P(C.dbd.O)(OM')2 the compounds and salts thereof are antibacterial agents.

REFERENCES:
patent: 4107304 (1978-08-01), Schrock et al.
patent: 4224442 (1980-09-01), Cooper
patent: 4337197 (1982-06-01), Gordon et al.
Woulfe, Tet. Letters, 25, 3293 (1984).
Atherton, Chem. Abs. 101, 6897.
Brewer et al., Chem. Abs. 101, 38265(g), 2-9-84.
Miller et al., J. Org. Chem. 47, 4828-33(1982).

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