Quinoline → HCID 88648589, compound

Participants

Reaction Conditions

Reaction Steps

100.0 g (0.38 mol) of monolauryl phosphoric acid and 134.4 g (1.13 mol) of thionyl chloride were charged in a reactor and heated under stirring at 50° C. for 4 hours under a nitrogen gas stream. After the reaction was completed, 100 ml of chloroform was added to dissolve the reaction product and 103.4 g (0.80 mol) quinoline was added and stirred. The solution was added dropwise at 0° C. under a nitrogen gas stream to a solution prepared by dissolving 157.5 g (0.46 mol) of benzyl-N-benzyloxycarbonyl serine into 100 ml of chloroform and cooled to 0° C. Stirring was effected at 0° C. for 4 hours and then the reaction temperature was raised to room temperature, at which temperature stirring was effected for another 4 hours. After the reaction was completed, the reactant was added with 100 ml of water and stirred at 20° C. for one hour. Then, the solvent was distilled off and the residue was extracted from diethyl ether. After washing the thus obtained ether layer with an aqueous solution of hydrochloric acid, ether was distilled off. The thus obtained residue was dissolved in methanol and reacted with hydrogen blown to the reactor under heating at reflux temperature of methanol at a normal pressure and in the presence of palladium/carbon catalyst for about 10 hours. Then, methanol was distilled off and the resultant residue was purified on silica gel column chromatography (eluent/chloroform:methanol=90:10). When 63.5 g of the thus obtained white solids were analyzed, the following results were obtained to prove that the compound is 2-amino-2-carboxyethyl-lauryl phosphoric acid (0.18 mol, yield 47.3%).

Provenance & Evidence