Reaktion #1856621

Reaktionsgleichung

N-(1-diethoxyphosphoryl-3-phenylpropyl) -leucine

3-(α-naphthyl) -L-alanine tert-butyl ester

1-hydroxybenzotriazole monohydrate

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

→

title compound

N-[N-(1-diethoxyphosphoryl-3-phenylpropyl)leucyl]-3-(α-naphthyl)-L-alanine tert-butyl ester

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat room temperature for 3 hours
2. 2
   Waschenthe diluted solution was washed with 15 ml of a saturated aqueous solution of sodium bicarbonate
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
5. 5
   Sonstigethe residue was separated
6. 6
   Sonstigepurified by silica gel chromatography (hexane: ethyl acetate=1:1)

Vorschrift

A solution of 61 mg of N-(1-diethoxyphosphoryl-3-phenylpropyl) -leucine and 39 mg of 3-(α-naphthyl) -L-alanine tert-butyl ester in 1.0 ml of dichloromethane was cooled to 0° C. Then 26 mg of 1-hydroxybenzotriazole monohydrate and 34 mg of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added to the solution which was stirred at 0° C. for 1 hour and then at room temperature for 3 hours. The reaction mixture was diluted with 15 ml of dichloromethane, and the diluted solution was washed with 15 ml of a saturated aqueous solution of sodium bicarbonate and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was separated and purified by silica gel chromatography (hexane: ethyl acetate=1:1) to yield the title compound as two mixtures each of which are composed of two stereoisomers (42 mg of a/b mixture, 35 mg of c/d/mixture). (iv) N-[N-(3-phenylphosphonopropyl)leucyl]-3-(α-naphthyl)-L-alanine

Quelle