Hydrochloric Acid → HCID 54562015, compound

Participants

Reaction Steps

To a solution of ethyl 2-fluoro-4-[[(8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl)carbonyl]amino]-benzoate (Compound 221, 135 mg, 0.25 mmol) in EtOH (5 mL) was added 20% aqueous NaOH (2 mL). The reaction mixture was stirred at room temperature overnight and acidified to pH 4 with 10% aqueous HCl. The EtOH was removed under reduced pressure and ethyl acetate and water were added to the residue. The organic layer was separated and washed with saturated NaHCO3, saturated aqueous NaCl, and dried over MgSO4. Concentration under reduced pressure afforded 110 mg (86%) of the title compound as a colorless solid. 1H NMR δ (acetone-d6) 8.09 (1H, d, J=2.1 Hz), 7.91 (1H, t, J=7.5 Hz), 7.68 (1H, d, J=2.1 Hz), 7.83 (1H, dd, J=12.8, 2.1 Hz), 7.50 (1H, dd, J=7.5 Hz, 2.1 Hz), 7.27 (4H, s), 5.87 (1H, s), 2.37 (3H, s), 1.56 (6H, s); MS (EI) m/e 511, 509, 496, 494, 452, 450, 357, 355, 312. Anal. (C26H21BrFNO4.0.6 H2O) C, H, N.

Provenance & Evidence