反应详情

温度

50 °C

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%).

1. temperatureheated
2. additionwas added
3. stirringstirred
4. additionThe solution was added dropwise at 0° C. under a nitrogen gas stream to a solution
5. customprepared
6. temperaturecooled to 0° C
7. stirringStirring
8. waitwas effected at 0° C. for 4 hours
9. temperaturethe reaction temperature was raised to room temperature, at which temperature
10. stirringstirring
11. waitwas effected for another 4 hours
12. stirringstirred at 20° C. for one hour
13. distillationThen, the solvent was distilled off
14. extractionthe residue was extracted from diethyl ether
15. washAfter washing the thus obtained ether layer with an aqueous solution of hydrochloric acid, ether
16. distillationwas distilled off
17. dissolutionThe thus obtained residue was dissolved in methanol
18. customreacted with hydrogen
19. temperatureunder heating
20. distillationThen, methanol was distilled off
21. customthe resultant residue was purified on silica gel column chromatography (eluent/chloroform:methanol=90:10)
22. customthe following results
23. customwere obtained