Synthesis of 3(s)-acylamino-1-[(phenyl)(1h-tetrazol-5-yl)amino]-2-azetidinones

Add time:08/15/2019    Source:sciencedirect.com

1-Phenyl 1 (1-benzyl-1H-tetrazol 5-yl)hydrazine has been synthesised from N1-benzyloxycarbonyl-N2-phenylhydrazide and benzyl isothiocyanate. Coupling with N-(benzyloxycarbonyl)-L-serine 3,4-dihydro-4-oxo 1,2,3-benzotriazin 3-yl ester and cyclisation of the product, using triphenyl phosphine and dimethyl azodicarboxylate, gave a fully protected β-lactam Hydrogenolytic deprotection and acylation gave the title compounds, which are related to Nocardicin A. Fast atom bombardment mass spectra showed (M + H)+ peaks for all the β-ldctams studied.

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