Trimethylsilyl triflate → HCID 88672369, compound

Participants

Reaction Steps

To a solution of 377 mg of (3S, 4R)-4-acetoxy-3-[(R)-1-(allyloxycarbonyloxy)ethyl]-1-(p-methoxybenzyl)-2-azetidinone in 2 ml of dry methylene chloride were added 448 mg (2 mmole) of 1-phenylthio-1-(trimethylsilyloxy)ethylene and then the mixture was stirred at room temperature, A catalytic amount of trimethylsilyltrifluoromethanesulphonate was added to the mixture, which was then left to stand at room temperature overnight. The precipitate produced was dissolved in 200 ml of ethyl acetate, and the resulting solution was washed successively with 100 ml of water and 100 ml of a saturated aqueous solution of sodium chloride. It was then dried over anhydrous magnesium sulphate and subjected to Lobar column chromatography eluted with a 1:1 by volume mixture of cyclohexane and ethyl acetate, to afford 430 mg (yield 91%) of the title azetidinone.

Provenance & Evidence