Process for synthesizing antibacterial cephalosporin compounds

Details Process for synthesizing antibacterial cephalosporin compounds Process for synthesizing antibacterial cephalosporin compounds

1990-04-27

1992-05-12

Bond, Robert T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540221, 540230, C07D50100, C07D50114

Patent

active

051129671

ABSTRACT:
A process for synthesizing 3-acryloxymethyl antibacterialcephalosporin compounds of formula ##STR1## wherein R is hydrogen or a carboxylic acid protecting group; R.sup.1 is hydrogen or an acyl group; R.sup.2 is hydrogen or lower alkoxy; and R.sup.3 is carbocyclic aryl substituted on the ring with one or more members selected from the group consisting of hydroxy, lower alkyl, amino, cyano, lower alkoxy, halogen and alkylcarboxy,
as well as the corresponding readily hydrolyzable esters, pharmaceutically acceptable salts and hydrates of these compounds where R is hydrogen, in which a 2-carboxylic acid 3-hydroxymethyl cephalosporin compound is first treated with an organic base to form an organic salt therewith, followed by acylation of the 3-hydroxymethyl substituent.

REFERENCES:
patent: 3445463 (1969-05-01), Van Heyningen
patent: 3532694 (1970-10-01), Somerfield et al.
patent: 4152432 (1979-05-01), Heymes et al.
J. Med. Chem., 8(1), 22 (1965), Van Heyningen.
J. Med. Chem., 13(6), 1114 (1970) Kokolja.
J. Antibio., 34(10), 1300 (1981) Takaya.
Derwent Abstract of EPA 295 630 (discloses no method of making).

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