Hydrochloric Acid → (S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-3-(3-chloro-4-isopropoxyphenyl)-5-(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1,2,4-oxadiazole (0.339 g, 0.762 mmol) in THF (15.24 ml) was added a solution of 1N HCl (1.524 ml, 1.524 mmol). After 48 h additional 1N HCl (2.286 ml, 2.286 mmol) was added and the reaction mixture was heated to 70° C. for about 2 h. After cooling to ambient temperature a solution of 1N NaOH (3.81 ml, 3.81 mmol) was added and the reaction mixture was concentrated in vacuo. The resulting solid was washed with copious amounts of water and dried in vacuo to provide (S)-3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol (0.294 g, 94%) as a colorless solid. LCMS (Table 1, Method c) Rt=2.73 min, m/z 405 (M+H)+.

Provenance & Evidence