Sodium hydride → HCID 59244623, compound

Participants

Reaction Steps

To a DMF suspension (1 ml) of (4-chloro-pyridin-2-yl)-carbamic acid tert-butyl ester (100 mg, 0.437 mmol), NaH (60% mineral oil dispersion, 68 mg) was added with ice cooling, followed by stirring at room temperature for 30 minutes. To the reaction mixture, bromoacetic acid methyl ester (0.19 ml, 2.06 mmol) was added, followed by stirring at room temperature for 1 hour. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate (20 ml×2). The organic layers were combined, and washed with saturated aqueous sodium chloride solution. After the organic layer was dried over magnesium sulfate, the magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10:1), to obtain [tert-butoxycarbonyl-(4-chloro-pyridin-2-yl)-amino]-acetic acid methyl ester as a colorless liquid (380 mg, 97%).

Provenance & Evidence