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  • Title: Epimerization of benzylpenicilloic acid in alkaline media.
    Author: Ghebre-Sellassie I, Hem SL, Knevel AM.
    Journal: J Pharm Sci; 1984 Jan; 73(1):125-8. PubMed ID: 6694069.
    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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