Trifluoroacetic acid → HCID 86745542, compound

Participants

Reaction Steps

To a solution of (Z)-3-[(2S,4S)-N-allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]acrylamide (1.02 g, 2.06 mmol) in methylene chloride (1 ml) were added trifluoroacetic acid (1 ml) and triethylsilane (0.33 ml, 2.07 mmol) under ice-cooling under nitrogen. The reaction mixture was stirred for 30 minutes at the same temperature, concentrated under reduced pressure, and diluted with methylene chloride (5 ml). The mixture was concentrated again, and extracted with ethyl acetate (50 ml). The organic layer was washed with 0.1M phosphate buffer (pH 5.7×2) and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated to give (Z)-3 [(2S,4S)-N-allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]acrylamide, which was used for the next reaction without purification. ##STR328##

Provenance & Evidence