Hydrochloric Acid → HCID 178442459, compound

Participants

Reaction Conditions

Reaction Steps

Hydrogen chloride (4 M in 1,4-dioxane) (2 mL, 8 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (192 mg, 0.39 mmol) in methanol (4 mL). After stirring at 70° C. for 1 h, volatiles were removed in vacuo. The residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded the title compound. Chiral HPLC eluting with IPA/heptane afforded the two individual enantiomers. 1H NMR (500 MHz, CD3OD) δ 8.47 (s, 1H), 7.82 (m, 1H), 7.73 (d, J=7 Hz, 2H), 7.64 (m, 1H), 7.07 (d, J=7 Hz, 2H), 6.58 (s, 1H), 3.19 (d, J=11 Hz, 1H), 3.13 (d, J=11 Hz, 1H), 2.40 (s, 2H), 1.61 (s, 3H), 1.62 (q, J=5.5 Hz, 2H), 0.87-0.75 (m, 9H); (M+H) found: 382.

Provenance & Evidence