3-Methylene cephalosporanic acid derivatives and process for pre

Details 3-Methylene cephalosporanic acid derivatives and process for pre 3-Methylene cephalosporanic acid derivatives and process for pre

1977-10-11

1979-02-06

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

2602391, 544 27, 544 28, C07D50102

Patent

active

041385535

ABSTRACT:
Novel substituted hydrazide derivatives of 7-(substituted)amino-3-methylene-cepham-4-carboxylic acids expressed by the formula ##STR1## wherein R.sub.1 represents alkyl containing at least 3 carbon atoms, cycloalkyl, or optionally substituted aryl, and one of R.sub.2 and R.sub.3 represents hydrogen with the other being hydrogen or the same as R.sub.1 ; or R.sub.1 and R.sub.2 form a heterocyclic ring optionally through a hetero atom together with the attached nitrogen and R.sub.3 represents hydrogen atom; and Z.sub.1 represents amino or protected amino; and acid addition salts thereof, which are useful as intermediates for synthesizing cephalosporin antibiotics. These compounds can be prepared in high yields from the corresponding substituted hydrazide derivatives of 6-substituted amino-1-oxide-2, 2-dimethyl-penam-3-carboxylic acids, which are readily available at low costs, by heating them in the presence of a thermal rearrangement promotor such as organic sulfonic acids and optionally in the further presence of a tertiary nitrogen-containing cyclic compound, followed if desired by splitting off the amino-protecting group and converting the product to acid addition salts.

REFERENCES:
patent: 3852295 (1974-12-01), Graham et al.
patent: 3879398 (1975-04-01), Ellerton et al.
patent: 3966720 (1976-01-01), Tomioka et al.
patent: 4075203 (1978-02-01), Chos

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