Process for 1-carba(dethia) cephalosporins

Details Process for 1-carba(dethia) cephalosporins Process for 1-carba(dethia) cephalosporins

1988-09-16

1990-07-03

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540364, C07D48704, C07D205085, C07B 3706

Patent

active

049392492

ABSTRACT:
The invention provides a free radical process for preparing 1-carba(1-dethia)cephalosporin antibiotics represented by the formula ##STR1## wherein R is amino or protected amino, R.sub.1 is H or alkoxy, R.sub.3 is H or alkyl, Z is ##STR2## where R.sub.2 is, e.g., H, halogen, or alkyl, or --CH.sub.2 R.sub.2 ' where R.sub.2 ' is, e.g., hydroxy, methoxy, or heterocyclicthio group, and A is a carboxy-protecting group which comprises heating a 2-substituted-methylcephalosporin 1,1-dioxide of the formula ##STR3## wherein R, R.sub.1, R.sub.3, and A are the same as in the formula above and Y is a free radical precursor group, e.g., C.sub.1 -C.sub.6 --Se--, C.sub.1 -C.sub.6 --S--, or phenyl--Se--; with a free radical initiator, e.g., a trialkyltin hydride, radiation, or a cobalt I salophen. Also provided are free radical compounds formed as intermediates in the process.

REFERENCES:
patent: 3660395 (1972-05-01), Wright
patent: 3660396 (1972-05-01), Wright
Kametani, T. et al., "Synthesis of Carbacepham and Carbacephem Ring Systems by Employing Radical Cyclization", Heterocycles, vol. 27, No. 4, 1988.
Kametani, T. et al., "Formation of Carbacephem Ring System By 1,6-Bond Coupling Through a Radical Cyclization Reaction", Heterocycles, vol. 19, No. 10, 1982.

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