Treatment of the derivative (5) of clavulanic acid with triethylamine leads to the endocyclic double bond isomer (6) and thence to the salt (10) which is a powerful inhibitor of β-lactamases; cleavage of the oxazoline ring of (6) with triethylamine or with pyridine gives the novel zwitterions (7) and (9) which are readily recyclised to (6) by thermolysis.
P. C. Cherry, C. E. Newall and N. S. Watson, J. Chem. Soc., Chem. Commun., 1978, 469 DOI: 10.1039/C39780000469
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