Hydrochloric Acid → HCID 66668997, compound

Participants

Reaction Conditions

Reaction Steps

Hydrogen chloride solution (4 M in 1,4-dioxane, 2 mL) was added to a solution of (R)-tert-butyl 4-(4-(3-(2-methylpyridin-4-yl)-3-oxo-1-o-tolylpropyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (example 372, step 1; 100 mg, 201 μmol). The reaction mixture was heated at 50° C. for 17 h, then partitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was dissolved in dichloromethane (5 mL), then cooled to 0° C. and treated with N,N-diisopropylethylamine (78 mg, 604 μmol) and methanesulfonyl chloride (34.6 mg, 302 μmol). The ice bath was removed, then after 3 h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) produced the title compound (24 mg, 25%). White foam, MS (ESI+): m/z=475.1 ([M+H]+).

Provenance & Evidence