Reaktion #367957

Reaktionsgleichung

L-glutamyl-L-prolyl-L-proline

Dibenzylphosphorylchloride carbon tetrachloride

triethylamine

triethylamine

→

dibenzylphosphoryl-L-glutamyl-L-prolyl-L-proline

Lösungsmittel

sodium bicarbonate

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto not more than 5° C.
2. 2
   workup.DISTILLATIONthe solution was distilled under reduced pressure
3. 3
   Sonstigeleaving a residue
4. 4
   Waschenwashed with ethyl acetate
5. 5
   Extraktionthe desired product was extracted with ethyl acetate
6. 6
   WaschenThe ethyl acetate phase was washed with sodium chloride solution
7. 7
   Trocknendried with anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONThe ethyl acetate was distilled off under reduced pressure
9. 9
   SonstigeThe residue was re-precipitated with ethyl acetate-ethyl ether

Vorschrift

The thus obtained amorphous L-glutamyl-L-prolyl-L-proline was dissolved in DMF (8 ml) and water (2 ml), and neutralized by addition of triethylamine (0.2 ml) while cooling to -5° C. Dibenzylphosphorylchloride carbon tetrachloride solution (3 m mole) and triethylamine were added dropwise to the mixture while keeping the temperature to not more than 5° C. and usually keeping the pH value to 8-9. The mixture was stirred for 3 hours at room temperature, and the solution was distilled under reduced pressure leaving a residue. The residue was dissolved in 5% sodium bicarbonate and then washed with ethyl acetate. The aqueous phase was acidified with 1N hydrochloric acid, and the desired product was extracted with ethyl acetate. The ethyl acetate phase was washed with sodium chloride solution and dried with anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure. The residue was re-precipitated with ethyl acetate-ethyl ether to obtain dibenzylphosphoryl-L-glutamyl-L-prolyl-L-proline (140 mg).

Quelle