6-Epi-hetacillin slowly hydrolyses in neutral aqueous solution to 6-epi-ampicillin, which then gradually cyclizes to 2-(3,6-dioxo-5-phenylpiperazin-2-yl)-5,5-dimethylthiazolidine-4-carboxylic acid by intramolecular nucleophilic attack of the side-chain amino-group upon the β-lactam carbonyl; under the same conditions hetacillin readily hydrolyses to yield ampicillin as sole product.
E. E. Roets, A. J. Vlietinck, G. A. Janssen and H. Vanderhaeghe, J. Chem. Soc., Chem. Commun., 1973, 484 DOI: 10.1039/C39730000484
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