Reaktion #1161199

Reaktionsgleichung

dicyclohexylamine

dioxane

o-nitrobenzene sulfonyl chloride

Nε -benzyloxycarbonyl-L-lysine

→

Nα -o-nitrobenzenesulfonyl-Nε -benzyloxycarbonyl-L-lysine dicyclohexylamine salt

Ausbeute 83.4%

Lösungsmittel

diethyl ether

sodium hydroxide

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was further stirred for 2.5 hours at room temperature
2. 2
   Sonstigeinsoluble matter was removed by filtration
3. 3
   SonstigeThe filtrate thus obtained
4. 4
   Waschenwas washed with two 100 ml portions of diethyl ether
5. 5
   workup.ADDITIONTo the water layer, ethyl acetate (150 ml) was added
6. 6
   SonstigeThe ethyl acetate layer was separated
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
9. 9
   Sonstigethe oily residue thus obtained
10. 10
    workup.STIRRINGTo the solution, with stirring

Vorschrift

Nε -benzyloxycarbonyl-L-lysine (4.42 g, 16 mmole) was dissolved in 1N aqueous sodium hydroxide (16 ml), and dioxane (10 ml) solution of o-nitrobenzene sulfonyl chloride (3.50 g, 16 mmole) was added dropwise to the solution while keeping the pH value thereof to between 10 and 11 with 1N aqueous sodium hydroxide while cooling with ice and stirring. The mixture was further stirred for 2.5 hours at room temperature, and insoluble matter was removed by filtration. The filtrate thus obtained was washed with two 100 ml portions of diethyl ether. To the water layer, ethyl acetate (150 ml) was added and the solution was adjusted to pH 1.0 with 1N aqueous hydrochloric acid under vigorous stirring. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the oily residue thus obtained was dissolved in diethyl ether (50 ml). To the solution, with stirring, dicyclohexylamine 2.99 g, 17 mmole) was added to obtain Nα -o-nitrobenzenesulfonyl-Nε -benzyloxycarbonyl-L-lysine dicyclohexylamine salt (yield:8.52 g; 83.4%)

Quelle