Trifluoroacetic acid → (E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]acrylamide

Participants

Reaction Steps

To a suspension of (E)-3-[(2S,4S)-N-allyloxycarbonyl 4-tritylthiopyrrolidin-2-yl]acrylamide (60 g, 120 mmol) in methylene chloride (60 ml) were added trifluoroacetic acid (60 ml) and triethylsilane (20 ml, 125 mmol) under ice-cooling. The reaction mixture was stirred under icecooling for 10 minutes and for additionally 30 minutes at room temperature, and concentrated. The residue was dissolved in methylene chloride (100 ml), and the solution concentrated. The obtained residue was dissolved ethyl acetate (750 ml), and the solution washed with 1M sodium phosphate buffer (pH 5.5, 500 ml and 250 ml×3) and saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The residue was dissolved in ethyl acetate (50 ml), treated with hexane (250 ml) to crystallize to give the title compound (30 g, 97.3% yield).

Provenance & Evidence