Carbon and oxygen analogs of penicillin

Details Carbon and oxygen analogs of penicillin Carbon and oxygen analogs of penicillin

C - Chemistry, Metallurgy

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260/118.5

C07D 499/00 (2006.01) C07C 45/00 (2006.01) C07F 9/535 (2006.01) C07F 9/54 (2006.01)

Patent

CA 1061332

ABSTRACT OF THE DISCLOSURE In accordance with this invention, it has been found that oxygen analogs of 6.beta.-aminopenicillanic acid and biologically active derivatives thereof can be formed from esters of 6-oxo- penicillanic acid. For example, 6.beta.-phenoxyacetoxypenicillanic acid - an oxygen 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 oxida- tion of the corresponding ester of 6.alpha.-hydroxypenicillanic acid. The oxygen analogs are formed by reducing the ester of 6-oxo- penicillanic acid to the corresponding 6.beta.-hydroxypenicillanate and then forming the desired analog by acylation.

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