Water → HCID 57991946, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of diethyl 2-(5-(5-((R)-3-(tert-butoxycarbonylamino)-4-(6-(trifluoromethyl)pyridin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)-2-nitrophenyl)malonate (165 mg, 242 μmol), water (4 μL, 242 μmol), and lithium chloride (51 mg, 1210 μmol) in DMSO (2 mL) was heated at 100° C. for 24 hours. The mixture was cooled to room temperature and partitioned between saturated aqueous NH4Cl (15 mL) and DCM (15 mL). The layers were separated, and the aqueous layer was extracted with DCM (2×15 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting yellow solid was dissolved in MeOH/DCM, absorbed onto silica gel, and purified by flash chromatography (silica gel, 40% to 70% EtOAc/hexanes) to provide ethyl 2-(5-(5-((R)-3-(tert-butoxycarbonylamino)-4-(6-(trifluoromethyl)pyridin-3-yl)butyl)-1,3,4-thiadiazol-2-yl)-2-nitrophenyl)acetate (117 mg, 79%) as a white solid. LCMS (API-ES) m/z: 610.0 (M+H+).

Provenance & Evidence