Preparation of the 7-oxo-4-oxa-1-azabicyclo[3.2.0]hept-2-ene system and the reversible cleavage of its oxazoline ring

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Abstract
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.

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