Tetrahydrofuran → 1-(4'-{1-methyl-5-[1-(3-trifluoromethyl-phenyl)-ethoxycarbonylamino]-1H-[1,2,3]triazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid

Participants

Reaction Steps

1-(4′-{1-Methyl-5-[1-(3-trifluoromethyl-phenyl)-ethoxycarbonylamino]-1H-[1,2,3]triazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid methyl ester (410 mg, 0.726 mmol) was dissolved 4 mL of THF and 4 mL of ethanol. To this stirred solution was added 1N sodium hydroxide solution (8 mL). The mixture was stirred at room temperature overnight. TLC indicated complete consumption of the starting material. The mixture was concentrated and the residue was dissolved in 15 mL of water. Dilute hydrochloric acid (1N, 9 mL) was added. The white solid was filtered and dried in the air to give 1-(4′-{1-methyl-5-[1-(3-trifluoromethyl-phenyl)-ethoxycarbonylamino]-1H-[1,2,3]triazol-4-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid (400 mg, 100% yield). LC/MS calcd for C29H25F3N4O4 (m/e) 550.0, obsd 551.0 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.29 (m, 2.6H), 1.44-1.52 (m, 2H), 1.60 (br d, 2.4H), 3.86 (s, 3H), 5.75-5.95 (br m, 1H), 7.43 (d, J=8.1 Hz, 2.5H), 7.61 (d, J=8.1 Hz, 2.5H), 7.69 (br m, 3.5H), 7.79 (d, J=7.6 Hz, 3.5H), 9.65 and 10.05 (br s, 1H), 12.35 (s, 1H).

Provenance & Evidence