Hydrochloric Acid → HCID 68774647, compound

Participants

Reaction Steps

To a stirred solution of (E)-tert-butyl 4-(4-(cyclohexyl-carbamoyl)phenoxy)-3-fluorobut-2-enylcarbamate (1.25 g, 3.1 mmol) in dichloromethane (54 mL) was added trifluoroacetic acid (6 mL). The reaction was then stirred at room temperature for 3 hours at which time TLC analysis showed no remaining starting material. Evaporation of the solvent and the remaining acid afforded a brown gum. Aqueous HCl (2 M; 5 mL) was then added and the reaction stirred for 40 minutes, upon which point an off-white solid had precipitated out of solution. Filtered, washing with ice cold aqueous HCl (1 M; 3 mL) and dried in a 60° C. oven to afford the title compound as an off-white powder (0.89 g, 85%); m.p.=210-212° C.; 1H-NMR (400 MHz, (CD3)2SO): δppm: 1.11 (1H, m), 1.15-1.33 (4H, m), 1.59 (1H, m), 1.70-1.77 (4H, m), 3.59 (2H, d, J 8.1 Hz), 3.71 (1H, m), 4.87 (2H, d, J 19.8 Hz), 5.52 (1H, dt, J 18.9, 7.8 Hz), 7.01 (2H, d, J 7.9 Hz), 7.83 (2H, d, J 7.9 Hz), 7.97-8.10 (3H, br s, NHs).

Provenance & Evidence