Hydrochloric Acid → 1-[4-(2,2-dimethylpropyl)-1H-imidazol-2-yl]-2-(4-pyridin-2-ylphenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

1.5 N Hydrochloric acid (1 mL) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-[1-hydroxy-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide (7 mg, 0.02 mmol) in tetrahydrofuran (1 mL). After heating in a sealed tube at 70° C. until no further reaction (LCMS), the reaction mixture was cooled to 0° C., quenched with 10% aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparative plate chromatography eluting with 15% methanol/ethyl acetate afforded the title compound. High pressure liquid chromatography (Chiralcel OD column) eluting with 20% isopropanol/heptane afforded the two pure enantiomers. (M+H) found: 336.

Provenance & Evidence