tert-butyl 1-(4-(5-(2-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate → HCID 56646206, compound

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Reaction Steps

A solution of tert-butyl 1-(4-(5-(2-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylate (46 mg, 80 μmol) in trifluoroacetic acid (1.5 mL) was stirred at room temperature for 75 min. Trifluoroacetic acid was removed under reduced pressure, followed by co-evaporation with ether. The crude product was purified by reversed-phase autoprep HPLC (Phenomenex S10 30×100 mm, 40 min gradient time, Detection Wave length 220 nm, Starting solvent: 10% aq. MeOH—0.1% TFA; Final solvent: 90% aq. MeOH—0.1% TFA) to obtain 1-(4-(5-(2-(4-(3-(trifluoromethyl)phenyl)tetrahydro-2H-pyran-4-yl)ethyl)-1,2,4-oxadiazol-3-yl)benzyl) azetidine-3-carboxylic acid (25 mg, 47% yield) as a white solid. LC/MS: m/e 516.19 (M+H)+. 1H NMR (400 MHz, CD3OD): δ ppm 8.09 (d, J=8.28 Hz, 2H), 7.66-7.75 (m, 2H), 7.62 (d, J=8.28 Hz, 2H), 7.49-7.59 (m, 2H), 4.50 (s, 2H), 4.29-4.42 (m, 4H), 3.87 (ddd, J=11.73, 5.46, 3.64 Hz, 2H), 3.72 (dt, J=16.75, 8.31 Hz, 1H), 3.45-3.63 (m, 2H), 2.60-2.79 (m, 2H), 2.32-2.36 (m, 2H), 2.27-2.32 (m, 2H), 1.90-2.08 (m, 2H).

Provenance & Evidence