تفاعل #1909784

معادلة التفاعل

N-tert-butoxycarbonyl-L-phenylalanine hydrochloride

aniline

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

hydroxybenzotriazole

→

N-tert-butoxycarbonyl-L-phenylalanylamino-benzene

المذيبات

dimethylformamide

Water

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with ethyl acetate
2. 2
   غسيلThe organic layer was washed successively with a 10% aqueous citric acid solution, water
3. 3
   تجفيفa saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled away under reduced pressure

الإجراء التجريبي

To a solution of N-tert-butoxycarbonyl-L-phenylalanine hydrochloride (2.65 g) and aniline (1.02 g) in dimethylformamide (DMF, 50 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC.HCl) and hydroxybenzotriazole (HOBT, 1.5 g) at room temperature, and the mixture was stirred for 6 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a 10% aqueous citric acid solution, water, a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure to give N-tert-butoxycarbonyl-L-phenylalanylamino-benzene. To a solution of the obtained compound in dichloromethane (20 ml) was added trifluoroacetic acid (10 ml) at room temperature, and the mixture was stirred for 1 hour. Toluene (10 ml) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. A 1M hydrogen chloride-ether solution (10 ml) was added to the residue, and crystallization gave the title compound (1.45 g, yield 52%).

المصدر