HCID 10505810, compound → HCID 67674084, compound

Participants

Reaction Steps

A mixture of 0.50 g (6R, 7S)-7-tert-butoxycarbonylamino-3-formyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (10) and 0.96 g rac-[2-oxo-1-(2,2,2-trifluoroethyl)-3-pyrrolidinyl]-triphenylphosphonium bromide in 6.0 ml 1,2 epoxybutane was heated to reflux for 6 h. The solvent was evaporated and the residue was purified by chromatography on silica gel using n-hexane:ethyl acetate=3:1 as eluent. The title compound, (E)-(6R, 7S)-7-tert-butoxycarbonylamino-8-oxo-3-[2-oxo-1-(2,2,2-trifluoro-ethyl)-pyrrolidin-3-ylidenemethyl]-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester, was obtained as white foam (0.55 g;78% Th).

Provenance & Evidence