CAS: 97033-11-9

(+/-)-4-tert-Butyl-azetidin-2-one is a chiral molecule with two stereocenters. It is an analogue of paclitaxel, which is a potent chemotherapeutic agent used in the treatment of cancer. Its high diastereoselectivity and organic chemistry make it an excellent candidate for synthesis of novel β-lactam derivatives. The (+) form of the molecule has been shown to have optimum steric properties for binding to β-lactamase enzymes, and can be synthesized from 1-(4′-methylphenyl)ethanone via a sequence of steps that include conversion to its bromide salt and then reacting with methyllithium followed by reaction with tert butyl azetidine hydrochloride. The (-) form can be synthesized from racemic 4-(3′,5′-dimethylphenyl)acrylic acid via the same sequence of steps.