Acetamidomalonic acid diethyl ester → HCID 21251139, compound

Participants

Reaction Steps

A mixture of diethyl acetamidomalonate (1.3 g, 6.0 mmol) and potassium tert-butoxide (0.73 g, 6.5 mmol) in N-methylpyrrolidone (30 mL) was stirred at room temperature for 30 min. 3-[4-(Bromomethyl)-3-ethoxyisoxazol-5-yl]-1-trityl-1H-1,2,4-triazole (2.8 g, 5.4 mmol) in N-methylpyrrolidone (20 mL) was added (temp 22-28° C.) and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was poured onto an ice/water mixture (250 mL) and the aqueous phase was extracted with EtOAc (3×250 mL). The organic extracts were washed with an aqueous solution of potassium tert-butoxide and brine, dried (Na2SO4) and concentrated in vacuo. Flash chromatography (silica gel, eluent: EtOAc/heptane/triethylamine=50:50:2) gave the title compound (2.2 g, 62%): mp 145-149° C.

Provenance & Evidence