Methanol → Methyl (3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-phenyl)acetate
Reaction equation
Cl.[Cl:2][C:3]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][C:4]=1[CH2:5][N:6]([CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1.[CH3:43]O>S(=O)(=O)(O)O>[CH3:43][O:19][C:18](=[O:20])[CH2:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:6]([CH2:5][C:4]2[CH:35]=[CH:36][CH:37]=[C:38]([C:39]([F:40])([F:41])[F:42])[C:3]=2[Cl:2])[CH2:21][CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (3-{3[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid hydrochloride salt (Example 1d, 0.1 g, 0.2 mmol) in methanol (2 ml) was added concentrated sulfuric acid (2 drops). After the resulting mixture was heated to reflux for 2 h solvent was removed under vacuum. The residue was dissolved in water and neutralized to pH=7. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with, brine, dried over magnesium sulfate, and concentrated in vacco to give 900 mg (93%) of the title compound as an oil. MS m/e 596.2 (M+H)+.