Triphenylphosphine → HCID 14074731, compound

Participants

Reaction Steps

A solution of 4-(triphenylmethylthio)-1-(benzyloxycarbonylchloromethyl)azetidin-2-one (850 mg), triphenylphosphine (640 mg) and 2,6-butidine (210 μl) in DMF (50 ml) was heated at 80° C. under nitrogen for 24 hours. The reaction was then cooled, diluted with ice water and extracted with ethyl acetate (2×100 ml). The ethyl acetate extracts were washed with water and brine, dried (Na2SO4) and evaporated. The residue was flash chromatographed with a solvent gradient of 15 to 60% ethyl acetate/hexane to afford recovered starting material (500 mg) and then 4-(triphenylmethylthio)-1-[(benzyloxycarbonyl)triphenylphosphoranylidenemethyl]azetidin-2-one (650 mg) as a white foam, Rf =0.20 (30% ethyl acetate/hexane).

Provenance & Evidence