Acetic Acid → (2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[2-(4-nitrobenzyloxycarbonylamino)ethyloxymethyl] pyrrolidine

Participants

Reaction Steps

To a solution of (2S,4S)-4-acetylthio-1-(4-nitrobenzyloxycarbonyl)-2-[2-(4-nitrobenzyloxycarbonylamino)ethyloxymethyl]pyrrolidine (0.59 g) in a mixture of methanol (12 ml) and tetrahydrofuran (12 ml) was added sodium methoxide (28% solution in methanol) (0.25 ml) at -20°~-10° 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 (0.1 ml) at -10°~0° C. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in ethyl acetate (20 ml). The solution was washed with water (20 ml), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on a silica gel (10 g) and eluted with a mixture of acetone and chloroform (5:95 V/V) to give (2S,4S)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)-2-[2-(4-nitrobenzyloxycarbonylamino)ethyloxymethyl] pyrrolidine (0.46 g).

Provenance & Evidence