Hydrochloric Acid → HCID 178442232, compound

Participants

Reaction Conditions

Reaction Steps

Hydrogen chloride (4 M in 1,4-dioxane) (108 mL, 433 mmol) was added to an ambient temperature solution of 3-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-1,1,1-trifluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]propan-2-ol (5.75 g, 8.7 mmol) in methanol (30 mL). After stirring at 70° C. for 1 h, volatiles were removed. The residue was partitioned between diethyl ether and 1N hydrochloric acid. The aqueous phase was washed with diethyl ether, basified with 2.5 N aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound. LCMS: 422 (M+H). High pressure liquid chromatography (Chiralcel AD-H column) eluting with 15% isopropanol/heptane afforded the two individual enantiomers (E1 and E2). 1H NMR (500 MHz, CDCl3) δ 8.52 (s, 1H), 7.87 (d, J=7.3 Hz, 2H), 7.67-7.65 (m, 3H), 7.48-7.45 (m, 2H), 6.56 (s, 1H), 3.46 (dd, J=15.1, 51.1), 2.33 (s, 2H), 0.80 (s, 9H).

Provenance & Evidence