Sodium hydride → HCID 90281999, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-{[(benzyloxy)carbonyl]amino}ethyl)benzoate (515 mg) in N,N-dimethylformamide (10.0 mL) was added 55% sodium hydride (65.0 mg) under ice-cooling, followed by stirring for 30 minutes under ice-cooling. Under ice-cooling, tert-butyl bromoacetate (0.300 mL) was added thereto, followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 4-(2-{[(benzyloxy)carbonyl](2-tert-butoxy-2-oxoethyl)amino}ethyl)benzoate (473 mg).

Provenance & Evidence