Tert-butyl 3-hydroxyazetidine-1-carboxylate → HCID 117667172, compound

Participants

Reaction Steps

To a mixture of tert-butyl 3-hydroxyazetidine-1-carboxylate (420 mg) and N,N-dimethylformamide (12.5 mL) was added potassium tert-butoxide (260 mg) under ice-cooling, followed by stirring for 1 hour, and then 3,5-dichloro-6-ethylpyrazine-2-carboxamide (500 mg) was added thereto, followed by stirring for 1 hour. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate), and then washed with a mixed solvent of hexane:diisopropyl ether to obtain tert-butyl 3-[(5-carbamoyl-6-chloro-3-ethylpyrazin-2-yl)oxy]azetidine-1-carboxylate (318 mg) as a white solid.

Provenance & Evidence