Methanol → HCID 25160450, compound

Participants

Reaction Conditions

Reaction Steps

To a 50-mL round-bottomed flask containing a magnetic stir bar were added water (2 mL) and OXONE® (155 mg, 0.252 mmol). The flask was cooled in an ice bath. A solution of Example 201 in methanol (11 mL) was added and the resulting slurry was stirred at 0° C. for 30 minutes. The mixture was allowed to warm to room temperature over 3 hours. The mixture was extracted with dichloromethane (3×5 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporator. The crude material was recrystallized from ethyl acetate/hexanes to afford the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ 1.62-1.67 (m, 4H), 1.76-1.88 (m, 4H), 1.98-2.02 (m, 2H), 2.33 (br s, 2H), 2.59-2.63 (m, 1H), 2.84 (t, J=4.8 Hz, 2H), 3.05 (s, 3H), 3.39 (t, J=6.6 Hz, 2H), 3.69-3.75 (m, 2H), 3.84 (t, J=5.4 Hz, 2H), 4.65 (br s, 2H), 7.48 (t, J=5.8 Hz, 1H), 11.94 (br s, 1H). MS (ESI+) m/z 453.1 (M+H)+. Anal. calcd. for C21H28N2O5S2: C, 55.73; H, 6.24; N, 6.19. Found: C, 55.76; H, 6.25; N, 6.10.

Provenance & Evidence