(alphaR,betaR)-beta-(2,5-Difluorophenyl)-beta-hydroxy-alpha-methyl-1H-1,2,4-triazole-1-butanethioamide → 2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol
反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C@@H:10](C)[C:11](N)=S>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([OH:21])([CH2:10][CH3:11])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1参加物
3
反応条件
- 温度
- 50 °C
実験手順
To a solution of (2R,3R)-3-(2,5-difluoro-phenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-ylthiobutyramide (106 g, 340 mmol) in EtOH (500 mL) warmed at 50° C. in a water-bath was added 4-cyano-2′-bromoacetophenone (78.4 g, 350 mmol) portionwise over a period of 15 min and the mixture was stirred for 2 h at 50° C. After evaporation of EtOH under reduced pressure, the residue was dissolved in EtOAc (1.2 L) and the solution was washed with sat. NaHCO3 and brine, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography followed by trituration with t-BuOMe to give pure (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl)]-2-(2,5-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol (117 g, 79%) as a white powdery crystal.