Hydrochloric Acid → HCID 86710371, compound

Participants

Reaction Steps

(S)-tert-Butyl (1-((9-(1-ethoxyvinyl)-4,6-dimethyl-5-oxo-5,6 dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (200 mg, 0.392 mmol) was treated with hydrochloric acid in 1,4-dioxane (981 μL, 3.92 mmol) at 0° C. The reaction mixture was allowed to stir at RT for 2 h and then evaporated to dryness. The crude material was neutralized with aqueous 10% NaHCO3 and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated which afforded (S)-9-acetyl-8-((2-amino-4-methylpentyl)oxy)-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.11 g, 0.164 mmol, 42% yield) as brown solid. The material was carried on without further purification. LC/MS (ESI) m/e 382.2 [(M+H)+, calcd for C22H28N3O3, 382.2]; LC/MS retention time (method E): tR=0.78 min.

Provenance & Evidence