Reaktion #1856619

Reaktionsgleichung

diethyl phosphite

L-leucine benzyl ester p-toluenesulfonate

3-phenylpropionaldehyde

triethylamine

→

title compound

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux in a Dean-Stark apparatus for 2 hours
3. 3
   Temperaturto cool
4. 4
   TemperaturThen the mixture was heated
5. 5
   Temperaturto reflux for 27 hours
6. 6
   Temperaturto cool
7. 7
   WaschenThe mixture was successively washed with 100 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of a saturated aqueous solution of sodium bicarbonate
8. 8
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
10. 10
    Sonstigethe residue was purified by silica gel chromatography (chloroform: ethyl acetate=10: 1, and hexane: ethyl acetate=1: 1)

Vorschrift

A mixture of 5.90 g of L-leucine benzyl ester p-toluenesulfonate, 2.01 g of 3-phenylpropionaldehyde and 2.09 ml of triethylamine in 100 ml of toluene was heated to reflux in a Dean-Stark apparatus for 2 hours. The mixture was allowed to cool, and then 1.93 ml of diethyl phosphite was added to the mixture. Then the mixture was heated to reflux for 27 hours, and then allowed to cool. The mixture was successively washed with 100 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (chloroform: ethyl acetate=10: 1, and hexane: ethyl acetate=1: 1) to yield the title compound as a mixture of stereoisomers, a light-yellow oil (1.87 g).

Quelle