Lithium Hydroxide → HCID 71455703, compound

Participants

Reaction Conditions

Reaction Steps

In a 250 ml, round-bottomed flask, 1-{3′-fluoro-4′-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazole-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid methyl ester (95 mg, 185 μmol) was combined with tetrahydrofuran (5 mL) and methanol (1.5 mL) to give a light yellow solution. 1M LiOH (1.85 mL, 1.85 mmol, Eq: 10) was added and the reaction was stirred at 25° C. for 22 h. The crude reaction mixture was concentrated in vacuo, acidified with 1M HCl and extracted with dichloromethane. The aqueous layer was back-extracted with dichloromethane (1×15 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 0% to 10% methanol in dichloromethane) to afford 85 mg (92%) of the desired product as a white powder. (M+H)′=501.1 (m/e). 1H NMR (DMSO-d6) δ ppm 12.39 (br. s., 1H), 9.92 (br. s., 1H), 7.64-7.78 (m, 3H), 7.59 (d, J=7.8 Hz, 2H), 7.37-7.50 (m, 5H), 7.02-7.37 (m, 2H), 5.74 (br. s., 1H), 3.89 (s, 3H), 1.41-1.60 (m, 4H), 1.09-1.32 (m, 3H).

Provenance & Evidence