Sodium hydride → HCID 57719188, compound

Participants

Reaction Steps

A 0° C. solution of compound [1-(4-methyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester (1.60 g, 5.8 mmol) in DMF (28 mL) is treated with sodium hydride (60% dispersion, 0.25 g, 6.4 mmol) and warmed to room temperature and stirred under N2 for 15 minutes. The resultant mixture is cooled to 0° C. and then treated with 1-propyl iodide (1.08 g, 6.4 mmol) and then warmed to room temperature and stirred for 30 minutes. The reaction is quenched with aqueous 1 N HCl (28 mL) and then worked up extractively with EtOAc and water. The organic layer is dried i and the solvent removed to give crude product that is purified by flash chromatography using a gradient of 10:1 to 1:1 hexanes:EtOAc to afford 1.40 g (76%) [1-(4-methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid methyl ester. 1H NMR. MS (ES+) Calc'd for C17H23N2O4 (M+1) 319. Found m/z 319 (100%).

Provenance & Evidence