Acetic Acid → HCID 24957692, compound

Participants

Reaction Steps

HOAc (0.05 mL, 0.88 mmol) and TBAF (0.3 mL, 0.37 mmol) are added to a solution of 1-{4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-imidazol-1-yl]-3,3-dimethyl-3,4-dihydro-2H-quinolin-1-yl}-2-phenyl-ethanone (115 mg) in THF (6 mL) at room temperature. The mixture is stirred at room temperature. In the next 4 h, TBAF (0.3 mL×2) are added and the mixture is stirred at room temperature for overnight. The reaction is adjusted by sat. NaHCO3 to basic and extracted into ethyl acetate and washed with brine; dried with anhydrous sodium sulfate and concentrated to give the crude compound, which is purified by reverse phase HPLC (CH3CN:H2O=10 to 80% over 20 mins) to the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.73 (s, 3 H), 0.97 (s, 3 H), 3.53 (br. s., 1H), 3.65 (d, J=13.1 Hz, 1 H), 3.83 (d, J=13.1 Hz, 1 H), 4.00 (s, 2 H), 4.70 (dd, 2 H), 5.30 (s, 1 H), 6.89-6.95 (m, 2 H), 7.03 (t, J=7.5 Hz, 1 H), 7.10 (s, 1 H), 7.24-7.37 (m, 6 H), 7.61 (br. s., 1 H).

Provenance & Evidence