反应详情

温度

0 °C

(S)-N-{3-[4-(1,1-Dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1) (2.0 g, 5.2 mmol) in 13 mL of CH2Cl2 and 13 mL of CH3CN is cooled to 0° C. Lithium t-butoxide (1.0 M in hexanes, 5.7 mL, 5.7 mmol) is added and the mixture is stirred at 0° C. for 25 min and then at RT for 10 min. The mixture is re-cooled to 0° C. and chloromethyl chloroformate (0.6 mL, 6.2 mmol) is added dropwise. The mixture is stirred for 10 min at 0° C. and then allowed to stir at RT overnight. The solution is diluted with CH2Cl2 and water and the layers are separated. The organic layer is washed with water, brine, dried over Na2SO4, and conc in vacuo. Purification by silica gel chromatography afforded the title compound in 74% yield (1.8 g). 1H NMR (400 MHz, CDCl3): δ 7.47 (dd, 1H), 7.22 (t, 1H), 7.13 (dd, 1H), 5.91 (d, 1H), 5.76 (d, 1H), 4.82 (m, 1H), 4.16 (m, 1H), 4.07 (m, 2H), 3.69 (dd, 1H), 3.10 (m, 5H), 2.58 (s, 3H), 2.38 (m, 2H), 2.17 (m, 2H). MS-APCI (m/z+): 341, 385, 477.

1. waitat RT for 10 min
2. temperatureThe mixture is re-cooled to 0° C.
3. stirringThe mixture is stirred for 10 min at 0° C.
4. stirringto stir at RT overnight
5. customthe layers are separated
6. washThe organic layer is washed with water, brine
7. dry with materialdried over Na2SO4
8. customPurification by silica gel chromatography