Triethylamine → 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]-N-methoxy-N-methylpropionamide

Participants

Reaction Steps

A suspension of 3-[5-(2,3-dihydro-1-benzofuran-5-yl)-1,3,4-oxadiazol-2-yl]propionic acid (3.00 g, 11.53 mmol), N,O-dimethylhydroxyamine hydrochloride (2.25 g, 23.06 mmol), triethylamine (4.0 mL, 28.83 mmol), 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (3.32 g, 17.30 mmol) and 1-hydroxybenzotriazole (2.34 g, 17.30 mmol) in N,N-dimethylformamide (50 mL) was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water, aqueous sodium hydroxide solution, hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (2.75 g, yield 79%) as colorless crystals.

Provenance & Evidence