Hydrochloric Acid → HCID 86636679, compound

Participants

Reaction Steps

Iron powder (48 mg, 853 μmol) was added to a suspension of ethyl 2-(5-(5-((R)-3-(tert-butoxycarbonylamino)-4-(6-(trifluoromethyl)pyridin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)-2-nitrophenyl)acetate (104 mg, 171 μmol) in EtOH (1.5 mL). 2N aqueous HCl (256 μL, 512 μmol) was added, and the mixture was heated under reflux for 4 hours. Saturated aqueous NaHCO3 (5 mL) was added dropwise and the mixture was stirred at room temperature for 5 minutes. It was diluted with H2O (5 mL) and extracted with DCM (3×15 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting light yellow oil was absorbed onto silica gel and purified by flash chromatography (silica gel, 2% to 6% MeOH/DCM) to deliver tert-butyl (R)-4-(5-(2-oxoindolin-5-yl)-1,3,4-thiadiazol-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (49 mg, 54%) as a white solid. LCMS (API-ES) m/z: 534.0 (M+H+).

Provenance & Evidence