Ammonium Hydroxide → (2R*,3R*)-N-[3-(2,4-Difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-2-butyl]-N-[4-(trifluoromethyl)benzoyl]glycinamide
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:29][N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)[C@@H:14]([CH3:15])[N:13]([C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:12][C:11](=O)[O:10]1.[OH-:35].[NH4+:36]>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:10])([CH2:29][N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)[C@H:14]([N:13]([C:16](=[O:27])[C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=1)[C:12](=[O:35])[CH2:11][NH2:36])[CH3:15]Participants
4
Procedure
To a solution of (5R*,6R*)-6-[2,4-difluorophenyl]-5-methyl-4-[4-(trifluoromethyl)benzoyl]-6-[(1H-1,2,4-triazol-1-yl)methyl]-2-morpholinone (0.5 g, 1 mmol) (obtained in example 29) in acetone (15 mL) was added dropwise 30% ammonium hydroxide (5 mL) and the mixture was stirred at room temperature during 1 h. The volatiles were removed under reduced pressure and the residue was partitioned between 1N NaHCO3 and chloroform. The organic phase was separated, dried over anhydrous sodium sulfate, the drying agent was filtered and the solvent removed in vacuo to afford the title product as a white solid (0.38 g, 80%).