反应详情

温度

100 °C

The product from Example 85A (0.110 g, 0.256 mmol) was dissolved in 3 mL of a 1:1 mixture of HOAc and 12 M aqueous HCl, and heated at 100° C. for 16 hours in a sealed vessel. The mixture was cooled to 0° C., diluted with 15 mL of water, and the pH was adjusted to ˜10 by the dropwise addition of 20% (w/v) aqueous KOH. The mixture was extracted three times with 25 mL of 5% n-propanol in CHCl3 and the combined extracts were dried over Na2SO4, filtered, and absorbed on silica gel. The crude material was chromatographed, eluting with 0-5% aqueous NH4OH in MeCN/MeOH (9:1), to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.91 (dd, J=3.7, 1.7 Hz, 1H), 7.64 (s, 4H), 7.52 (d, J=8.8 Hz, 2H), 7.21-7.27 (m, 1H), 7.07 (dd, J=9.5, 1.7 Hz, 1H), 6.65 (d, J=8.8 Hz, 2H), 4.10-4.19 (m, 1H), 3.56-3.67 (m, 1H), 3.23-3.35 (m, 1H), 2.91-3.22 (m, 5H), 2.15-2.32 (m, 1H), 2.12 (br s, 1H), 1.87 (ddd, J=12.9, 7.5 Hz, 1H). MS (ESI+) m/z 359 (M+H)+.

1. temperatureThe mixture was cooled to 0° C.
2. extractionThe mixture was extracted three times with 25 mL of 5% n-propanol in CHCl3
3. dry with materialthe combined extracts were dried over Na2SO4
4. filtrationfiltered
5. customabsorbed on silica gel
6. customThe crude material was chromatographed
7. washeluting with 0-5% aqueous NH4OH in MeCN/MeOH (9:1)