Trifluoroacetic acid → HCID 69287216, compound

Participants

Reaction Steps

A solution of tert-butyl(1R,3R,4S)-3-(hydroxymethyl)-4-(2-(3-(trifluoromethyl)-benzamido)acetamido)cyclohexyl(isopropyl)carbamate (130 mg) in CH2Cl2 is treated with CF3COOH (7 ml) and stirred at room temperature for 2 hours. The solution was evaporated and the residue neutralized with 1 N NaOH and extracted into CH2Cl2. The extract was washed with water, brine, dried over Na2SO4, filtered and the solvent evaporated to give 100 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ(TMS): 8.12 (s, 1 H), 8.03 (d, J=7.8 Hz, 1 H), 7.94 (bt, 1 H), 7.75 (d, J=7.8 Hz, 1 H), 7.57 (t, J=7.8 Hz,l H), 7.39 (bd, 1 H), 4.31 (m, 1 H), 4.26 (dd, J=5 Hz, J=16 Hz, 1 H), 4.13 (dd, J=5 Hz, J=16 Hz, 1 H), 3.42 (m, 1 H), 3.27 (m, 1 H), 3.05 (m, 1 H), 2.84 (m, 1 H), 1.92-1.60 (m, 8 H), 1.12 (d, J=6.3 Hz, 6 H). MS found: (M+H)+=416.38.

Provenance & Evidence