Under basic conditions, methyl benzyl-5-epipenicillinate 1,1-dioxide (6, X = SO2, R = NH.CO.CH2Ph) undergoes epimerisation at positions 6 and 3, giving the sulphones (7; X = SO2, R = NH.CO.CH2Ph) and (10), and β-elimination to yield (3R,4R)-1-(1-methoxycarbonyl-1-methylprop-1-enyl)-3-phenylacetamidoazetidin-2-one-3-sulphinic acid (9; X = SO2H).
C. M. Pant and R. J. Stoodley, J. Chem. Soc., Chem. Commun., 1977, 57 DOI: 10.1039/C39770000057
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