Hydrochloric Acid → HCID 66668997, compound

Participants

Reaction Steps

Hydrogen chloride solution (4 M in 1,4-dioxane, 1.5 mL, 6.0 mmol) was added at room temperature to a solution of (R)-tert-butyl 4-(4-(3-(2-methylpyridin-4-yl)-3-oxo-1-o-tolyl-propyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (example 372, step 1; 200 mg, 403 μmol) in 1,4-dioxane (4 mL), then after 2 h the reaction mixture was evaporated. The residue was suspended in dichloromethane (8 mL), then treated with N,N-diisopropylethylamine (312 mg, 2.42 mmol) and methanesulfonyl chloride (92 mg, 805 μmol) at 0° C. The ice bath was removed, then after 16 h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane. The organic layer was dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient, then dichloromethane-methanol 9:1) gave the title compound (27 mg, 16%; light brown foam, MS (ESI+): m/z=411.2 ([M+H]+)) and (R)-3-[4-(1-methane sulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (66 mg, 35%).

Provenance & Evidence