反应详情

tert-Butyl bis(2-hydroxyethyl)carbamate (Aldrich; 600 mg, 2.92 mmol) was dissolved in dichloromethane (30 mL), and stirred overnight at room temperature after adding oleic acid (Tokyo Chemical Industry Co., Ltd.; 1.82 g, 6.43 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.72 mmol), and 4-dimethylaminopyridine (89 mg, 0.731 mmol). The aqueous layer was extracted with ethyl acetate after adding a saturated sodium bicarbonate aqueous solution to the reaction mixture. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100) to give tert-butyl N,N-bis(2-((Z)-octadec-9-enoyloxy)ethyl)carbamate (1.26 g, 58.7%).

1. extractionThe aqueous layer was extracted with ethyl acetate
2. additionafter adding a saturated sodium bicarbonate aqueous solution to the reaction mixture
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. filtrationafter filtration
7. customThe resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100)