반응 #738764

반응 방정식

N-t-butoxycarbonyl-(2-cyanophenyl)alanine

dihexylamine

1-hydroxybenzotriazole monohydrate

N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride

→

N-t-butoxycarbonyl-(2-cyanophenyl)alanine dihexylamide

수율 79.1%

용매

N,N-dimethylformamide

water

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   세척The extract was washed with 5% aqueous potassium bisulfate solution
3. 3
   건조a saturated aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate
4. 4
   기타After removal of the drying agent
5. 5
   여과by filtration
6. 6
   농축the filtrate was concentrated under reduced pressure
7. 7
   기타The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=4:1)

실험 절차

To a solution of 0.81 g of the crude N-t-butoxycarbonyl-(2-cyanophenyl)alanine and 0.67 g of dihexylamine in 8 ml of N,N-dimethylformamide were added 0.55 g of 1-hydroxybenzotriazole monohydrate and 0.69 g of N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride, followed by stirring at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 5% aqueous potassium bisulfate solution, a saturated aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=4:1) to give 1.01 g of N-t-butoxycarbonyl-(2-cyanophenyl)alanine dihexylamide.

출처