FC(F)(S(F)(=O)=O)[C:3](F)(F)[C:4](F)(F)[C:5]([F:8])(F)F.[F:18][C:19]1[N:24]=[C:23]([N:25]2[C@@H](CO)C[O:27][C:26]2=[O:32])[CH:22]=[CH:21][N:20]=1.F.F.F.C(N(CC)CC)C.C(N(CC)CC)C>C1COCC1.O>[F:8][CH2:5][C@H:4]1[CH2:3][O:32][C:26](=[O:27])[N:25]1[C:23]1[CH:22]=[CH:21][N:20]=[C:19]([F:18])[N:24]=1Perfluorobutanesulfonyl fluoride (0.18 mL, 0.98 mmol, 4 equiv) was added to a solution of (S)-3-(2-fluoropyrimidin-4-yl)-4-(hydroxymethyl)oxazolidin-2-one (52 mg, 0.24 mmol) in THF (1.2 mL) at room temperature. Triethylamine trihydrofluoride (0.16 mL, 0.98 mmol, 4 equiv) and triethylamine (0.41 mL, 3.0 mmol, 12 equiv) were then added and the solution was stirred at 40° C. for 18 hours. The reaction was then cooled to room temperature and diluted with water (25 mL). The mixture was extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (10 mL), dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane) provided (R)-4-(fluoromethyl)-3-(2-fluoropyrimidin-4-yl)oxazolidin-2-one (0.021 g, colorless oil) in 40% yield. 1H NMR (400 MHz, CDCl3) δ 8.53 (dd, J=5.7, 2.1 Hz, 1H), 8.18 (dd, J=5.7, 3.7 Hz, 1H), 5.08-4.93 (m, 2H), 4.91-4.72 (m, 1H), 4.66-4.55 (m, 2H). MS m/z 215.9 (M+H)+; Rt-0.57 min.
Wird geladen…
