Acetic Acid → HCID 25001822, compound

Participants

Reaction Steps

Methyl 3-(2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoate (83 mg, 0.181 mmol) was dissolved in ethanol (4mL) and NaOH (4mL, 8.00 mmol) was added. The mixture was stirred at room temperature under nitrogen. After 20 minutes the reaction was neutralized by drop-wise addition of acetic acid. The aqueous mixture was then frozen and lyophilized. The solid obtained after lyophilization was brought up in DCM, filtered, and washed with DCM. The filtrate was concentrated and brought up in ether to provide a slightly cloudy solution. IN HCl in ether was added dropwise until white precipitate formed. Material was collected by filtration, washed with ether, and dried in a vacuum oven to give 3-(2-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)propan-2-ylamino)propanoic acid as the hydrochloric acid salt (61.5 mg; 70.6%). LCMS (Table 1, Method f) Rt=1.98 min, m/z=444.29 (M+H)+; 1H NMR (400 MHz, DMSO-d6)δ ppm 8.32 (d, J=8.57 Hz, 2H), 8.12 (d, J=2.08 Hz, 1H), 8.03 (dd, J=8.64, 2.10 Hz, 1H), 7.85 (d, J=8.59 Hz, 2H), 7.25 (d, J=8.78 Hz, 1H), 4.79 (sept, J=6.11 Hz, 1H), 2.95 (t, J=6.20 Hz, 2H), 2.44 (t, J=6.17 Hz, 2H), 1.84 (s, 6H), 1.40 (d, J=6.04 Hz, 6H).

Provenance & Evidence