反应详情

A solution of sodium nitrite (0.033 g, 0.478 mmol) in water (2.171 mL) was added to an ice bath chilled solution of Example 45H (0.14 g, 0.434 mmol) in hypophosphorous acid, solution in water (9.03 mL, 87 mmol, 9.63M) and HCl (2.140 mL, 26.1 mmol, 12.2M). A sample was taken out after 10 minutes, quenched with 1M NaOH(aqueous), and the reaction was determined to be complete by LC/MS. The reaction mixture was allowed to reach room temperature and was poured into 100 mL 1M NaOH(aqueous). Additional 1M NaOH(aqueous) was added until the pH=14. The product was extracted with dichloromethane three times, dried over sodium sulfate, and the solvent was evaporated. The residue was then purified by reverse phase HPLC to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.03 (s, 1H), 8.19 (t, J=5.8, 1H), 7.61-7.50 (m, 5H), 7.50-7.39 (m, 2H), 7.11 (t, J=7.3, 1H), 7.04 (d, J=7.9, 1H), 4.47 (s, 2H), 3.37-3.10 (m, 6H), 3.02 (dd, J=6.5, 14.9, 1H); MS (ESI+) m/z 308.0 (M+H)+.

1. customquenched with 1M NaOH(aqueous)
2. customto reach room temperature
3. additionwas poured into 100 mL 1M NaOH(aqueous)
4. additionAdditional 1M NaOH(aqueous) was added until the pH=14
5. extractionThe product was extracted with dichloromethane three times
6. dry with materialdried over sodium sulfate
7. customthe solvent was evaporated
8. customThe residue was then purified by reverse phase HPLC