Trifluoroacetic acid → HCID 56646838, compound

Participants

Reaction Steps

(E)-tert-butyl 1-(4-(5-(2-(1-(3,4-difluorophenyl)cyclohexyl)vinyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (59 mg, 0.110 mmol) was dissolved in TFA (2 mL, 26.0 mmol), and the mixture was stirred for 30 mins at room temp. The acid was evaporated off, and the residue was dissolved in 2 mL of DMF and was purified by preparative LC/MS with the following conditions: Column: Waters SunFire C18, 19×250 mm, 5-μm particles; Guard Column: Waters XBridge C18, 19×10 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient: 15-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing product were combined and dried via centrifugal evaporation. (E)-1-(4-(5-(2-(1-(3,4-difluorophenyl)cyclohexyl)vinyl)-1,2,4-oxadiazol-3-yl)benzyl) azetidine-3-carboxylic acid was obtained as a waxy solid (28.7 mg, 54.3% yield). LC/MS: m/e 479.7 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.95 (2H, d, J=8.28 Hz), 7.55 (1H, ddd, J=12.99, 7.97, 2.38 Hz), 7.39-7.48 (3H, m), 7.31 (1H, ddd, J=6.46, 4.33, 2.01 Hz), 7.15 (1H, d, J=16.31 Hz), 6.50 (1H, d, J=16.56 Hz), 3.65 (2H, s), 3.44 (2H, br. s.), 3.25 (3H, m), 2.08 (4H, m), 1.47 (6H, m).

Provenance & Evidence