Hydroquinone → HCID 13219905, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 190 mg (0.25 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-1-(p-nitrobenzyloxyethyl)-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone, 250 mg (1.5 mmole) of triethyl phosphite and 10 mg (0.90 mmole) of hydroquinone in 20 ml of toluene was heated at 95° C. for 15 hours. On thin layer chromatography, disappearance of the starting materials and appearance of 1-(N-methylformimidoyl)pyrrolidin-3-yl, (3S,4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triethoxyphosphoranylidenemethyl]-4-([(S)-1-(p-nitrobenzyloxy-carbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone and the desired carbapenem compound were observed. The solvent and excess triethyl phosphite were evaporated off under reduced pressure. To the oily residue were added 20 ml of toluene and the mixture was heated at 95° C. For 57 hours to complete the cyclization reaction of the phosphoranylidene compound. After evaporation of the solvent, the residue was purified with a Lobar column. The fraction eluted with a 2:1 by volume mixture of benzene and ethyl acetate was collected and 151.5 mg (yield 83%) of the title compound was obtained as an oil.

Provenance & Evidence