反应详情

温度

100 °C

To compound 385-A (0.388 g, 0.87 mmol) was added acetic anhydride (10 mL) and 85% H3PO4 (0.10 mL), and the reaction was heated at 100° C. for three days. Additional acetic anhydride (10 mL) was added, the reaction mixture heated for an additional 4 more days. The reaction mixture was cooled, concentrated under vacuum, partitioned between EtOAc (100 mL) and saturated NaHCO3 (50 mL), filtered, the organic layer washed with brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography (SiO2) eluting with an EtOAc-heptane gradient to afford 0.197 g of compound 385-B as a colorless oil. 1H-NMR (DMSO-d6): δ 2.64 (s, 3H), 2.91-2.72 (m, 2H), 4.01-3.87 (m, 5H), 7.54-7.43 (m, 2H), 7.87 (d, 2H), 7.99-7.92 (m, 1H), 8.19-8.08 (m, 3H); MS: m/z 486.1 (MH+).

1. temperaturethe reaction mixture heated for an additional 4 more days
2. temperatureThe reaction mixture was cooled
3. concentrationconcentrated under vacuum
4. custompartitioned between EtOAc (100 mL) and saturated NaHCO3 (50 mL)
5. filtrationfiltered
6. washthe organic layer washed with brine (50 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude residue was purified by flash column chromatography (SiO2)
11. washeluting with an EtOAc-heptane gradient