Dimethyl Sulfoxide → HCID 86753541, compound

Participants

Reaction Steps

110 mg (0.87 mmole) of oxalyl chloride were dissolved in 5 ml of methylene chloride. To the solution was added 137 mg (1.75 mmole) of dimethyl sulphoxide under a stream of a nitrogen gas at -780° C. The mixture was then stirred for 10 minutes, after which a solution of 500 mg (0.577 mmole) of (3R, 4R)-1-[1-hydroxy-1-(p-nitrobenzyloxycarbonyl)methyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidin-3-ylthio]carbonylmethyl)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-azetidinone was added to the mixture over 2 minutes. The mixture was stirred for 5 minutes and then 250 mg (2.48 mmole) of triethylamine were added thereto and the mixture was stirred for 15 minutes. About 30 ml of a 0.1M phosphate buffer solution (pH 7.1) was added to the mixture, which was then stirred and extracted with methylene chloride. The extract was dried over anhydrous magnesium sulphate and the solvent was distilled off. The residue was quickly subjected to column chromatography through 10 g of silica gel eluted with 2:1 to 1:1 by volume mixtures of benzene and ethyl acetate, to afford 350 mg (yield 70%) of the title product as an oily substance. Infra-red and nuclear magnetic resonance spectra of the product agreed with those of the product obtained as described in Example 16(a)(iii).

Provenance & Evidence