Hydrochloric Acid → (2S,4R)-2-(2,4-dioxoimidazolidin-1-yl)methyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
반응식
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([CH2:27][N:28]2[CH2:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])[CH2:10]1)(C(C)(C)C)(C)C.Cl>CO>[O:34]=[C:29]1[NH:30][C:31](=[O:33])[CH2:32][N:28]1[CH2:27][C@@H:11]1[CH2:10][C@@H:9]([OH:8])[CH2:13][N:12]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15]참가 물질
4
반응물 2
생성물 1
시약·촉매·용매 1
실험 절차
A solution of (2S,4R)-4-t-butyldimethylsilyloxy-2-(2,4-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (4.78 g) in a mixture of methanol (100 ml) and conc. hydrochloric acid (1.62 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was evaporated in vacuo. The resulting residue was dissolved in toluene (30 ml) and the solution was concentrated under reduced pressure to give a residue. The residue was chromatographed on silica gel (60 g) eluting with a mixture of dichloromethane and acetone (2:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-2-(2,4-dioxoimidazolidin-1-yl)methyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3.27 g).