Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1977-03-21
1979-03-06
Rizzo, Nicholas S.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
424270, 2602391, C07D27704
Patent
active
041430468
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:
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patent: 3799939 (1974-03-01), Rapoport
patent: 3809700 (1974-05-01), Rapoport
patent: 4053408 (1977-10-01), Holden
Lo et al., JACS 94 8253, (1972).
Lo et al., J. Org. Chem. 40 191, (1975).
Lo Young S.
Sheehan John C.
Conlin David G.
Massachusetts Institute of Technology
Rizzo Nicholas S.
Smith, Jr. Arthur A.
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