3-{1-[4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3-hydroxymethyl-butyryl]-piperidin-4-yl}1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one → 2-(4-Amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyraldehyde
反応式
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][CH:13]([CH2:35][OH:36])[CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:29][CH2:28][C:27]4[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=4[NH:25][C:24]3=[O:34])[CH2:19][CH2:18]2)=[O:16])=[CH:4][C:3]=1[Cl:37]>ClCCl>[NH2:1][C:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][C:5]([CH2:12][CH:13]([CH2:14][C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[CH2:29][CH2:28][C:27]4[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=4[NH:25][C:24]3=[O:34])[CH2:21][CH2:22]2)[CH:35]=[O:36])=[CH:4][C:3]=1[Cl:37]参加物
3
反応物 1
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of 0.539 g (1.000 mmol) 3-{1-[4-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-3-hydroxymethyl-butyryl]-piperidin-4-yl}1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one (Intermediate product 35) in 10 mL dichloromethane was added 0.933 g (2.200 mmol) Dess-Martin-Periodinane and the mixture was stirred for 3 hours at RT. The reaction mixture was washed with sat. aqueous sodium thiosulphate solution and sat. aqueous NaCl solution, dried over sodium sulphate and evaporated down i. vac. The crude product was purified by column chromatography (silica gel, gradient dichloromethane/MeOH 50:1→25:1 v/v).