Hydrochloric Acid → 2-((3R)-1-(2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetic acid

Participants

Reaction Steps

To a mixture of ethyl 2-((3R)-1-(2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetate (72 mg, 0.126 mmol) in acetonitrile (5 mL) was added 6N HCl (5 mL). The reaction mixture was stirred at room temperature for 3 days. The reaction mixture was filtered and purified by HPLC. HPLC conditions: PHENOMENEX® Luna C18 5 micron column (250×30 mm); 25-100% CH3CN/water (0.1% TFA); 25 minute gradient; 30 mL/min. Isolated fractions with correct mass were freeze-dried overnight to yield 66 mg of 2-((3R)-1-(2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidin-3-yl)acetic acid as a TFA salt. 1H NMR (400 MHz, MeOH-d3) δ ppm 8.12 (2H, d, J=8.35 Hz), 7.71 (2H, d, J=7.47 Hz), 7.49-7.66 (5H, m), 5.16 (1H, dd, J=9.67, 4.39 Hz), 3.81 (1H, d, J=11.86 Hz), 3.56 (1H, d, J=11.42 Hz), 3.14-3.33 (2H, m), 2.83-2.94 (1H, m), 2.72 (1H, t, J=11.86 Hz), 2.16-2.38(3H, m), 1.78-1.92 (3H, m), 1.10-1.33 (1H, m). MS (m+1)=543. HPLC Peak RT=3.24 minutes (Analytical Method A). Purity=98%.

Provenance & Evidence