Reaction #738764

Reaction equation

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

dihexylamine

1-hydroxybenzotriazole monohydrate

N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride

→

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

Yield 79.1%

Solvents

N,N-dimethylformamide

water

Conditions

Workup

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

Procedure

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.

Source