Dichloromethane → 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylic acid
Reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:23])[C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCl>>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:23])[C:8]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
3
Procedure
To a solution of tert-butyl 3-cyclohexyl-2-(2-(2-methoxy-2-oxoethoxy)phenyl)-1-methyl-1H-indole-6-carboxylate 26 (0.7 g, 1.46 mmol), in dichloromethane 50 mL tri-fluoro-acetic acid (4.2 g, 36.6 mmol) was added. The resulting mixture was stirred at room temperature for 12 hours. The solvent was removed then the residue was purified by column chromatography using dichloromethane/methanol to yield 0.59 g (96%) of 3-cyclohexyl-2-[2-(2-methoxy-2-oxoethoxy)phenyl]-1-methyl-1H-indole-6-carboxylic acid 27: m/z=422 (M+H)+.