Lithium hydroxide, monohydrate → (S)-2-Hydroxy-2-phenyl-N-quinolin-3-yl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-acetamide

反応式

[C:1]1([C@H:7]([O:33]C(=O)C)[C:8](=[O:32])[N:9]([C:22]2[CH:23]=[N:24][C:25]3[C:30]([CH:31]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O1CCCC1.O>[OH:33][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([N:9]([C:22]1[CH:23]=[N:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=1)=[O:32]

参加物

実験手順

To a solution of 155 mg acetic acid (S)-phenyl-{quinolin-3-yl-[2-(4-trifluoromethyl-phenyl)-ethyl]-carbamoyl}-methyl ester in tetrahydrofuran (6.0 mL) were added 3.0 mL water and 20 mg lithium hydroxide monohydrate. The mixture was stirred at room temperature for 2 h. The mixture was diluted with water and extracted 3 times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide the title compound. MS(m/e): 451.1 [M+H]+.