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Epimerization of benzylpenicilloic acid in alkaline media

I Ghebre-Sellassie, S L Hem, A M Knevel

Journal of Pharmaceutical Sciences

|January 1, 1984

Abstract:

5R,6R-Benzylpenicilloic acid was found to epimerize slowly in alkaline media to 5S,6R-benzylpenicilloic acid until equilibrium was established. Epimerization proceeded via the imine tautomer of penamaldic acid rather than the enamine form and was found to favor the 5S,6R-epimer at equilibrium. The conversion process was monitored using both reverse-phase high-performance liquid chromatography and NMR spectroscopy.

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