Potassium Carbonate → (1-Naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester

Participants

Reaction Steps

A solution of (2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester (6.48 g, 37.6 mmol) in DMF (250 mL) is treated with 2-(bromomethyl)-napthalene (9.15 g, 41.4 mmol), MgSO4 (4.53 g, 37.6 mmol) and then K2CO3 (15.61 g, 0.113 mol) at 0° C. The resultant mixture is warmed to room temperature and stirred under N2 for 16 hours. The reaction mixture is filtered, and then aqueous 1N HCl (300 mL) is added to the filtrate. The filtrate is extracted with Et2O and the organic layer dried. The solvent is removed to give a crude oil which is purified by flash chromatography using 2:1 hexanes:acetone to afford 6.27 g of (1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester (53%). Rf=0.32 (1:1 hexanes:acetone). 1H NMR.

Provenance & Evidence