反应详情

To a solution of compound 10a (33 g, 56 mmol) in dry DMSO (100 mL) was added sodium thiomethoxide (4.0 g, 56 mmol) under nitrogen. The reaction mixture was heated to 1000 C under nitrogen for 1 hour. Another 0.28 eq. of sodium thiomethoxide (1.1 g, 16 mmol) was added, and the reaction mixture was heated to 1000 C under nitrogen for 1 hour. The reaction mixture was cooled and partitioned between ethyl ether and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried with sodium sulfate, filtered and concentrated. The crude product was purified with a flash chromatography on silica gel eluted with 50% ethyl acetate in hexane to yield compound 10b as a pale yellow solid (27 g, 44 mmol, 78%). HPLC-MS (CI) m/z=524.1 (M+H+-Boc), tR=3.134 (method 4). 1H NMR (CDCl3): 1.38 (s, 9H), 2.07 (s, 3H), 2.51 (s, 3H), 3.90 (s, 3H), 4.07-4.13 (m, 1H), 4.29-4.39 (m, 1H), 5.30-5.53 (m, 2H), 5.79-5.85 (m, 1H), 6.80-6.91 (m, 2H), 6.70 (dd, 1H), 7.06-7.15 (m, 2H), 7.22-7.41 (m, 6h ).

1. temperatureThe reaction mixture was heated to 1000 C under nitrogen for 1 hour
2. temperaturethe reaction mixture was heated to 1000 C under nitrogen for 1 hour
3. temperatureThe reaction mixture was cooled
4. custompartitioned between ethyl ether and water
5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
6. dry with materialdried with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product was purified with a flash chromatography on silica gel
10. washeluted with 50% ethyl acetate in hexane