[H-].[Na+].[CH3:3][N:4]1[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[C:6]([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[N:5]1.S(C1C=CC(C)=CC=1)(O[CH2:23][C@@H:24]1[O:26][CH2:25]1)(=O)=O.[Cl-].[NH4+]>O.CN(C)C=O>[CH3:3][N:4]1[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:23][C@H:24]3[CH2:25][O:26]3)[CH:13]=2)=[N:5]1
Add sodium hydride (0.14 g, 0.0059 mol) at 0° C. under nitrogen to a stirred solution of 3-(1-methyl-1H-thieno[3,2-c]pyrazol-3-yl)phenol (example 3) (1.13 g, 0.0049 mol) and dimethylformamide (50 mL). Stir 15 min. and add (R)-(−)-glycidyl tosylate (1.12 g, 0.0049 mol, Aldrich Chemical Company), and then stir overnight at room temperature. Pour into water (400 mL), add a little ammonium chloride and extract with ethyl acetate. Dry (Na2SO4), filter and evaporate the extract, and purify the residue by flash chromatography (silica gel, elute with dichloromethane and then with 2% methanol in dichloromethane). Concentrate the desired fractions to afford the title compound as a white solid (0.85 g, 60% yield).
Wird geladen…
