Acetic Acid → HCID 86650663, compound

Participants

Reaction Steps

Add water (490 mL) and trifluoroacetic acid (126 mL, 1.67 mol) sequentially to a solution of 1-(4-trifluoromethoxy-phenyl)-3-(R)-1-phenyl-ethylamino)-5(R)-phenyl-1,5-dihydro-pyrrol-2-one (245 g, 558 mmol) in toluene (1.22 L). Stir at ambient temperature for 2 hours. Add water (1.0 L) and discard the aqueous layer. Wash the organic layer with 1N HCl (500 mL×2). To the organic layer add HOAc (10 mL, 174 mmol) and 1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamine (170 g, 836 mmol). Heat to 40° C. for 18 hours. Add water (400 mL), separate and discard the aqueous layer. Wash the organic layer with water (500 mL) and concentrate the organic layer to a dark oil. Dissolve the residue in toluene (400 mL) and concentrate to a brown paste. Triturate the solid with 20% MTBE/hexanes (1.0 L). Filter the mixture and collect the title compound as white solid (190 g, 65%). 1H NMR (400 MHz, DMSO-d6) δ 8.01 (m, 1H), 7.83 (d, J=8 Hz, 1H), 7.69 (d, J=8 Hz, 1H), 7.64 (d, 12 Hz, 2H), 7.26 (d, J=8 Hz, 2H), 7.17 (m, 3H), 7.03 (d, J=8 Hz, 2H), 5.78 (s, 1H), 5.73 (s, 1H), 4.70 (s, 1H), 1.62 (s, 3H), 1.59 (s, 3H) LC-MS ESI m/z: 522 (M+H)+, Tr=6.53 min., method 1.

Provenance & Evidence