A ceph-3-emcarboxylic acid reacted with diphenylphosphoryl azide–toluene–t-butyl alcohol–triethylamine to give the 4α- and 4β-t-butoxycarbonylceph-2-ems and a 4-t-butoxyformamidoceph-2-em. Interconversion studies on the 4α- and 4β-esters were performed. Reaction in the presence of excess of sodium azide gave as the sole β-lactam product a 4-t-butoxyformamidoceph-3-em.
M. M. Campbell, A. Henderson and S. J. Ray, J. Chem. Soc., Perkin Trans. 1, 1979, 1659 DOI: 10.1039/P19790001659
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