Treatment of p-methoxybenzyl 6β-(triphenylmethylamino)penicillanate (Ia) with methyl iodide and strong anhydrous base caused selective cleavage of the thiazolidine ring to give 1-(1-p-methoxybenzyloxycarbonyl-2-methylprop-1-enyl)-4R-methylthio-3R-(triphenylmethylamino)azetidin-2-one (IIa) which was converted into analogues of pencillins containing a non-fused β-lactam ring.
J. P. Clayton, J. H. C. Nayler, R. Southgate and P. Tolliday, J. Chem. Soc. D, 1971, 590 DOI: 10.1039/C29710000590
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