5-chloro-1H-indole-7-carboxylic acid [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amide → 5-Chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-hydroxy-phenyl)-ethyl]-amide
反応式
C([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][N:17]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:33][CH:32]=2)[C:18]([C:20]2[CH:21]=[C:22]([Cl:29])[CH:23]=[C:24]3[C:28]=2[NH:27][CH:26]=[CH:25]3)=[O:19])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:37]([C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:17]([CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)[C:18]([C:20]2[CH:21]=[C:22]([Cl:29])[CH:23]=[C:24]3[C:28]=2[NH:27][CH:26]=[CH:25]3)=[O:19])=[CH:32][CH:33]=1)([CH3:40])([CH3:38])[CH3:39]参加物
4
実験手順
200 mg of 5-chloro-1H-indole-7-carboxylic acid [2-(3-benzyloxy-phenyl)-ethyl]-(4-tert-butyl-benzyl)-amide (0.36 mmol) were dissolved in 20 ml EtOAc and hydrogenated for 5 h over 20 mg Pd/C 10%. After removal of the catalyst by filtration, the solution was concentrated in vacuo and the residue purified by column chromatography (8 g silicagel, heptane/EtOAc 2:1) leading to 136 mg of 5-chloro-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-hydroxy-phenyl)-ethyl]-amide (79%) as a light yellow solid. MS (ISP) 461.4 (M+H)+.