Diethyl Ether → HCID 56644161, compound

Participants

Reaction Steps

A solution of tert-butyl 1-(4-(5-(((1-(4-fluorophenyl)cyclohexyl)methoxy)methyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (37 mg, 69 mol) in trifluoroacetic acid (1.5 mL) was stirred at room temperature for 2 h. Trifluoroacetic acid was removed under reduced pressure, followed by co-evaporation with ether to obtain a solid which was stirred with ether (7 mL) for 3.5 h, filtered and dried to obtain 1-(4-(5-(((1-(4-fluorophenyl)cyclohexyl)methoxy)methyl)-1,2,4-oxadiazol-3-yl)benzyl) azetidine-3-carboxylic acid (26 mg, 63% yield) as a white solid. LC/MS: m/e 480.21 (M+H)+. 1H NMR (400 MHz, CD3OD): δ ppm 8.17 (d, J=8.03 Hz, 2H), 7.65 (d, J=7.78 Hz, 2H), 7.43 (dd, J=8.28, 5.52 Hz, 2H), 7.02 (t, J=8.53 Hz, 2H), 4.68 (s, 2H), 4.52 (s, 2H), 4.38 (d, J=7.53 Hz, 4H), 3.72 (ddd, J=16.63, 8.78, 8.47 Hz, 1H), 3.59 (s, 2H), 2.05-2.30 (m, 2H), 1.68-1.88 (m, 2H), 1.48-1.69 (m, 3H), 1.27-1.47 (m, 3H).

Provenance & Evidence