Hydrochloric Acid → HCID 178483310, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (±)-tert-butyl 1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)ethyl(methyl)carbamate and (±)-tert-butyl 1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)ethyl(methyl)carbamate (95 mg, 0.130 mmol) in MeOH (326 μL) was mixed with 4 M HCl in dioxane (0.65 mL, 2.61 mmol) and the reaction stirred at 50° C. for 0.5 h. The reaction mixture was cooled to rt and diluted with 2 M aq. Na2CO3, brine and EtOAc. The products were extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 40:60) to give the title compound. MS (ESI) m/z 496.34(M−1).

Provenance & Evidence