Carbon Dioxide → HCID 57719683, compound

Participants

Reaction Steps

1.6 g of Ethyl 3-(4-{[(t-butoxycarbonyl)amino]methyl}-phenyl)-2-isopropoxypropanoate was dissolved in 10 ml of 4N hydrogen chloride-dioxane solution. After stirring was continued at room temperature for 1 hour, the solution was concentrated, to give 1.4 g of ethyl 3-[4-(ammoniomethyl)-phenyl]-2-isopropoxypropanoate hydrochloride. Next, 25 mg of the obtained ethyl 3-[4-(ammoniomethyl)phenyl]-2-isopropoxypropanoate chloride was dissolved in 0.8 ml of N,N-dimethylformamide which was saturated with carbon dioxide by adding dry ice, and 65 mg of cesium carbonate and 74 mg tetrabutylammonium iodide were added, and the mixture was stirred at room temperature for 30 minutes. Then 41 mg of 4-chlorobenzyl bromide was added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water. The solvent was concentrated, and the residue was treated with 1.0 ml of ethanol and 0.2 ml of 5N sodium hydroxide, and the mixture was stirred at room temperature for 3 hours. Then the solution was neutralized with 2N hydrochloric acid, extracted with ethyl acetate, and the solvent was removed. The residue was purified by reverse-phase high performance liquid chromatography, to give 9.27 mg of the title compound.

Provenance & Evidence