反应详情

To (R)-acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid chloromethyl ester (10) (751.8 mg, 1.58 mmol) and sodium iodide (236.0 mg, 1.58 mmol) in acetonitrile (30 mL), is added the cesium salt of N-BOC-isonipecotic acid (884.2 mg, 2.45 mmol). The mixture is heated to reflux overnight. After cooling to RT, the mixture is filtered and washed with dichloromethane. The filtrate is diluted with CH2Cl2 and water and the layers are separated. The aq layer is extracted with dichloromethane twice and the combined organic layers are washed with water, brine, dried over sodium sulfate and conc in vacuo. Purification by silica gel chromatography gave the title compound in 72% yield (757.3 mg, 1.13 mmol). 1H NMR (400 MHz, CDCl3): δ 7.47 (dd, 1H), 7.24 (t, 1H), 7.14 (dd, 1H), 5.88 (s, 2H), 4.78-4.85 (m, 1H), 4.18 (dd, 1H), 4.08 (t, 2H), 4.03 (dd, 2H), 3.67 (dd, 1H), 3.13-3.20 (m, 4H), 3.10 (dt, 1H), 2.83 (t, 2H), 2.60 (tt, 1H), 2.59 (s, 3H), 2.35-2.46 (m, 2H), 2.17-2.23 (m, 2H), 1.90-1.96 (m, 2H), 1.57-1.686 (m, 2H) 1.45 (s, 9H). MS-APCI (m/z+): 570.

1. temperatureThe mixture is heated
2. temperatureto reflux overnight
3. filtrationthe mixture is filtered
4. washwashed with dichloromethane
5. additionThe filtrate is diluted with CH2Cl2 and water
6. customthe layers are separated
7. extractionThe aq layer is extracted with dichloromethane twice
8. washthe combined organic layers are washed with water, brine
9. dry with materialdried over sodium sulfate and conc in vacuo
10. customPurification by silica gel chromatography