反应详情

To a stirred solution of (1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethanol (0.500 g, 1.45 mmol) and 3-nitrobenzoic acid (0.242 g, 1.45 mmol) in dichloromethane (15.0 mL) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.560 g, 2.91 mmol) and N,N-dimethylpyridin-4-amine (0.089 g, 0.73 mmol). The reaction was stirred at room temperature for 16 hours. The reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (25.0 mL) and extracted with dichloromethane (×2). The combined organic extracts were dried on magnesium sulphate, filtered and the solvent removed in vacuo to afford a yellow oil. The crude material was purified by silica gel chromatography eluting sequentially with iso-hexane, ethyl acetate and 10% methanol in ethyl acetate to afford the title compound as a yellow solid (0.642 g, 90% yield).

1. customThe reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (25.0 mL)
2. extractionextracted with dichloromethane (×2)
3. customThe combined organic extracts were dried on magnesium sulphate
4. filtrationfiltered
5. customthe solvent removed in vacuo
6. customto afford a yellow oil
7. customThe crude material was purified by silica gel chromatography
8. washeluting sequentially with iso-hexane, ethyl acetate and 10% methanol in ethyl acetate