Isolation, structure elucidation, and synthesis of novel penicillin degradation products: thietan-2-ones

Abstract

High-field nuclear magnetic resonance spectroscopy, mass spectrometry, infrared spectroscopy, and ultraviolet spectroscopy were used to determine the structures of two novel degradation productions of the penicillins sodium nafcillin (1) and sodium oxacillin (2). The degradation products of compounds (1) and (2) were found to possess the novel thietan-2-one structures (3)and (4), respectively. The structure of compound (4) was confirmed by chemical synthesis via two independent routes. The structure of compound (3) was confirmed by single-crystal X-ray crystallography.