Trichloroacetyl isocyanate → (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonyloxymethyl-4-acetylthiopyrrolidine
反応式
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][OH:22])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:25][C:26]([Cl:33])([Cl:32])[C:27]([N:29]=[C:30]=[O:31])=[O:28]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][O:22][C:30]([NH:29][C:27](=[O:28])[C:26]([Cl:33])([Cl:32])[Cl:25])=[O:31])=[O:11])=[CH:23][CH:24]=1)([O-:3])=[O:2]参加物
4
実験手順
(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-acetylthiopyrrolidine (100 mg) was dissolved in 3 ml of dry ethyl acetate. To the solution was added 0.05 ml of trichloroacetyl isocyanate under ice-cooling in a nitrogen stream, followed by stirring at the same temperature for 1 hour. The mixture was diluted with ethyl acetate, washed successively with a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to obtain (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonyloxymethyl-4-acetylthiopyrrolidine.