Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

To tert-butyl 1-(4-(5-(2-(1-(3,4-difluorophenyl)cyclohexyl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (50.1 mg, 0.093 mmol) was added trifluoroacetic acid (2 mL, 26.0 mmol), and the mixture was stirred for 30 mins. The acid was evaporated off to give an oily residue. It was purified by preparative HPLC (Column: Phen-Luna 5u C18 21.2×100 mm, Sol A: 10% MeOH—90% H2O—0.1% TFA, Sol B: 90% MeOH—10% H2O—0.1% TFA, Start % B: 50, Final % B: 100, Gradient Time: 10 mins) to give pure 1-(4-(5-(2-(1-(3,4-difluorophenyl)cyclohexyl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid, TFA (40.5 mg, 0.067 mmol, 71.5% yield) as a foamy solid. LC/MS: m/e 482.14 (M+H)+. 1H NMR (400 MHz, CCl3D) δ ppm 12.51 (1H, br. s.), 8.02 (2H, d, J=7.03 Hz), 7.47 (2H, d, J=7.91 Hz), 6.98-7.21 (3H, m), 4.28-4.62 (4H, m), 4.01-4.24 (2H, m), 3.53-3.83 (1H, m), 2.49-2.68 (2H, m), 1.94-2.18 (4H, m), 1.21-1.72 (8H, m).

Provenance & Evidence