L-Alanine → HCID 53955669, compound

Participants

Reaction Steps

To a solution of 4.64 g. (0.052 mol) of L-alanine and 9.24 g. (0.11 mol) of sodium bicarbonate in 100 ml. of water there was added 10.4 g. (0.036 mol) of 3-benzoyl-2-methylpropionic acid, N-hydroxysuccinimide ester. Dioxane (50 ml.) and tetrahydrofuran (50 ml.) were added and the mixture stirred at room temperature for 2 days. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane and dilute hydrochloric acid. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give 10.0 g. of a yellow gum. The gum was chromatographed on silica gel with ethyl acetate-hexane-acetic acid (75:25:1) as solvent to give 4.4 g. of a solid intermediate compound. The solid was reprecipitated from hexane-ether to give a white solid. To the preceding compound (0.01 mol) in 25 ml. of acetic acid there can be added (0.01 mol) of bromine. After stirring 18 hours, the solvent can be removed and the residue reacted with 0.01 mol of potassium thioacetate in acetonitrile for 24 hours. The solvent can be removed in vacuo to obtain N-[3-acetylthio-3-(benzoyl)-2-methylpropionyl]-L-alanine as a glass.

Provenance & Evidence