4-Nitrobenzyl chloroformate → HCID 86753537, compound

Participants

Reaction Conditions

Reaction Steps

125 mg (0.194 mmole) of (3S, 4R)-3-[(R)-1-hydroxyethyl]-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]-carbonylmethyl)-1-[2-methyl-1-(p-nitrobenzyloxycarbonyl)-prop-1-enyl]-2-azetidinone were dissolved in 4 ml of methylene chloride. To the solution were added, in turn, 71 mg (0.58 mmole) of 4-(N,N-dimethylamino)-pyridine and 126 mg (0.58 mmole) of p-nitrobenzyloxy-carbonyl chloride, with stirring at 0° C. The reaction mixture was then stirred at room temperature for 1 hour, after which it was diluted with methylene chloride and washed with a saturated aqueous solution of sodium chloride. The solvent was distilled off and the residue was subjected to chromatography using a Lobar column B eluted with a 2:3 by volume mixture of hexane and ethyl acetate, to afford 82 mg (yield 51%) of the title product as an oily substance. Infra-red and nuclear magnetic resonance spectra of the product agreed with those of the product of Preparation 7.

Provenance & Evidence