反应详情

温度

70 °C

A suspension of Example 1D (0.25 g, 1.1 mmol) in dioxane (3 mL) was sequentially treated with triethylamine (0.17 mL, 1.2 mmol) and triphosgene (0.11 g, 0.37 mmol), heated to 70° C. for 2 hours, and concentrated. The concentrate was resuspended in THF (3 mL), treated with N-methyltoluidine, stirred at room temperature for 18 hours, and partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography with 2% methanol/dichloromethane to give 76 mg (20% yield) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 2.34 (s, 3H); 3.27 (s, 3H); 4.50 (s, 2H); 7.08 (d, J=7.46 Hz, 1H); 7.12 (d, J=8.48 Hz, 1H); 7.17 (s, 1H); 7.31 (t, J=7.80 Hz, 1H); 7.48 (d, J=8.82 Hz, 2H); 7.57 (d, J=8.82 Hz, 3H); 7.62 (d, J=3.39 Hz, 1H); 7.65 (d, J=5.76 Hz, 1H); 8.24 (s, 1H); 8.64 (s, 1H). MS (ESI(+)) m/e 372 (M+H)+.

1. concentrationconcentrated
2. additiontreated with N-methyltoluidine
3. custompartitioned between water and ethyl acetate
4. extractionThe aqueous phase was extracted with ethyl acetate
5. washthe combined extracts were washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography with 2% methanol/dichloromethane