Trifluoroacetic acid → HCID 44183931, compound

Participants

Reaction Steps

To a mixture of the product of step 3 (34.8 mg, 0.074 mmol) in dry dichloromethane (3 mL) at 0° C. under nitrogen was added trifluoroacetic acid (1.0 mL, 13 mmol). All solids dissolved immediately upon addition of trifluoroacetic acid. the solution was stirred for 1.5 ours at which time LC-MS analysis showed reaction complete. The reaction was concentrated under vacuum and the residue was triturated with ether to remove excess trifluoroacetic acid and organic impurities. The resulting sticky solid was dried under vacuum and stored in the freezer overnight. The crude product was purified by HPLC on a Phenomenex Synergi Polar-RP 80A column to afford the impure title compound as a white solid after lyophilization. The solid was triturated with acetonitrile (3×) to afford the pure title compound as a white solid. LC-MS (negative ionization) m/e 369 (M−H); LC-MS (positive ionization) m/e 354 (M+H—NH3); 1H NMR (600 MHz, D2O; unreferenced) (δ, ppm) 7.53 (2H, d, J=8.5 Hz), 7.46 (2H, d, J=8.5 Hz), 4.23 (2H, br s), 4.11 (2H, s), 3.39 (1H, d, 3=12 Hz), 3.18 (1H, d, J=12 Hz), 2.27-2.31 (1H, m), 2.09-2.14 (1H, m), 1.90-2.00 (1H, m), 1.813-1.89 (1H, m).

Provenance & Evidence