Hydrochloric Acid → HCID 53495669, compound

Participants

Reaction Steps

(R/S)-tert-Butyl 2-(2-hydroxy-2-(4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamido)acetate (Example 56, 30 mg, 0.055 mmol) was dissolved in THF (3 mL) and MeOH (1.50 mL). Next, LiOH (2.64 mg, 0.110 mmol) was added. After 20 min, additional LiOH (2.64 mg, 0.110 mmol) was added. After another 20 min, 1N HCl was used to adjust the pH to 4-5. The reaction mixture was concentrated. EtOAc was added and the resulting mixture was filtered. The filtrate was concentrated to provide (R/S)-2-(2-hydroxy-2-(4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamido)acetic acid (15 mg, 0.029 mmol, 52.2% yield): LCMS=488.2 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.47 (1 H, s), 8.13 (2 H, d, J=8.35 Hz), 7.53-7.75 (7 H, m), 5.17 (1 H, s), 3.99 (2 H, s); HPLC peak RT=7.1 min (Method A).

Provenance & Evidence