Acetic Acid → HCID 86742942, compound

Participants

Reaction Steps

To a solution of (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (8.20 g) in methanol (82 ml) was added sodium methoxide (28% solution in methanol) (5.7 ml) at -10°-0° C. in a nitrogen stream and the mixture was stirred at the same condition for 1 hour. To the mixture was added glacial acetic acid (1.9 ml) at -10°-0° C. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate (100 ml). The solution was washed with water (100 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (75 g) and eluted with a mixture of methanol and chloroform (2:98 V/V) to give (2S,4S)-1-allyloxycarbonyl-4-mercapto-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (6.89 g)

Provenance & Evidence