Carbon analogs of penicillin

Details Carbon analogs of penicillin Carbon analogs of penicillin

1981-02-17

1982-11-30

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424270, 424271, C07D49900, A61K 31425

Patent

active

043615147

ABSTRACT:
In accordance with this invention, it has been found that carbon and oxygen analogs of 6.beta.-aminopenicillanic acid and biologically active derivatives thereof can be formed from esters of 6-oxopenicillanic acid. For example, 6.beta.-phenoxyacetoxypenicillanic acid--an oxygen analog of penicillin V and 6.beta.-phenoxyacetylmethylpenicillanic acid--a carbon analog of penicillin V, may be formed from an ester of 6-oxopenicillanate. The ester of 6-oxopenicillanic acid is formed by a diiospropyl carbodiimide/dimethyl sulfoxide oxidation of the corresponding ester of 6.alpha.-hydroxypenicillanic acid. The oxygen analogs are formed by reducing the ester of 6-oxopenicillanic acid to the corresponding 6.beta.-hydroxypenicillanate and then forming the desired analog by acylation. The carbon analogs are formed by a Wittig reaction of the ester of 6-oxopenicillanic acid with a suitable acylmethylenetriphenylphosphorane followed by saturation of the newly formed double bond and removal of the protective ester group.

REFERENCES:
patent: 4053468 (1977-10-01), Holden
patent: 4224579 (1980-11-01), Barth
patent: 4282149 (1981-08-01), Sheehan et al.

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