Dimethylformamide → HCID 71279203, compound

Participants

Reaction Steps

5-[2-Bis(tert-butoxycarbonyl)aminoethyl]-3-phenyl-[1,2,4]triazole (96 mg, 247 μmol; example 22, step 1) and potassium carbonate (85.4 mg, 618 μmol) were combined with DMF (1 mL) and the mixture was stirred for 30 min at RT. 1-Bromo-2-methoxyethane (34.3 mg, 23.2 μL, 247 μmol) was added and the mixture was stirred at 60° C. for 16 h. The reaction mixture was cooled down to RT, a second portion of 1-bromo-2-methoxyethane (34.3 mg, 23.2 μL, 247 μmol) and potassium carbonate (34.2 mg, 247 μmol) were added and the mixture was stirred at 60° C. for another 4 h. The reaction mixture was poured into ethyl acetate (25 mL) and the organic phase was washed with water (3×10 mL) and brine (1×15 mL). The aqueous layers were back-extracted with ethyl acetate (1×25 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to give 120 mg crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as colorless oil (29 mg, 83.7 μmol, 33.9%).

Provenance & Evidence