Water → HCID 178522239, compound

Participants

Reaction Steps

To a solution of 19b (0.1 g, 0.21 mmol) in 5 mL of CH3CN was added lithium hydroxide (15.4 mg, 0.64 mmol) followed by 2 mL of water at room temperature. The reaction mixture was stirred overnight. The solvent was evaporated in vacuo and washed with EtOAc. The aqueous layer was acidified with 1N HCl to give white precipitates. The resulting white solids were collected by suction filtration and washed with water. The crude product was recrystallized from MeOH to give the titled compound (0.84 g, 90%) as a white solid. mp 210-212° C. 1H NMR (DMSO-d6): 12.60 (s, 1H), 8.48 (s, 1H), 7.87 (d, J=8 Hz, 1H), 7.47 (d, J=9 Hz, 1H), 7.21 (d, J=9 Hz, 1H), 7.03 (d, J=8 Hz, 1H), 6.35 (d, J=8 Hz, 1H), 4.66-4.57 (m, 1H), 3.73-3.60 (m, 1H), 1.87-1.50 (m, 1H). 13C NMR (DMSO-d6): □ 167.04, 160.90, 154.36, 141.99, 139.84, 131.48, 122.77, 121.67, 118.57, 115.28, 71.95, 45.66, 27.71, 27.36. MS (ESI) m/z: 439.1 (M+H+). Anal. Calcd for C21H21F3N2O5: C, 57.53; H, 4.83; N, 6.39. Found: C, 57.33; H, 4.81; N, 6.29.

Provenance & Evidence