Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1978-09-27
1981-08-04
Rizzo, Nicholas S.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
424270, C07D49900
Patent
active
042821495
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.-phenoxyacetoxy-penicillanic 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.
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Lo Young S.
Sheehan John C.
Conlin David G.
Massachusetts Institute of Technology
Neuner George W.
Rizzo Nicholas S.
Smith, Jr. Arthur A.
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