4-Nitrobenzyl chloroformate → HCID 86753539, compound

Participants

Reaction Conditions

Reaction Steps

56 mg (0.079 mmole) of (3S, 4R)-3-[(R)-1-hydroxyethyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidin-3-ylthio]carbonylmethyl)-1-[2-methyl-1-(p-nitrobenzyloxycarbonyl)prop-1-enyl]-2-azetidinone were dissolved in 1.5 ml of methylene chloride. To the solution were added, in turn, 29 mg (0.24 mmole) of 4-(N,N-dimethylamino)pyridine and 51 mg (0.24 mmole) of p-nitrobenzyloxycarbonyl chloride, with stirring at 0° C. The reaction mixture was stirred at room temperature for 3 hours, diluted with methylene chloride, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulphate. The solvent was distilled off and the residue was subjected to thin layer chromatography using silica gel, developed with a 1:5 by volume mixture of hexane and ethyl acetate, to afford 30 mg (yield 42%) of the title product as an oily substance. 8 mg (14%) of the starting material was also recovered.

Provenance & Evidence