Reaktion #318111

Reaktionsgleichung

2-(tert-butoxycarbonylamino)-2-methylpropionate

1-(benzyloxycarbonyl)piperazine

1-hydroxybenzotriazole

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

hydrochloric acid

→

title compound

Ausbeute 67.8%

1-(2-Amino-2-methylpropionyl)-4-(benzyloxycarbonyl)piperazine hydrochloride

Ausbeute 67.8%

Lösungsmittel

N,N-dimethylformamide

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with ethyl acetate
2. 2
   WaschenThe extract was washed with water, 1 mol/L aqueous sodium hydroxide solution, water and brine successively
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   workup.ADDITIONTo the residue was added 4 mol/L hydrochloric acid (1,4-dioxane solution, 25 mL)
6. 6
   workup.STIRRINGthe mixture was stirred at room temperature for 4 hours
7. 7
   workup.ADDITIONTo the reaction mixture was added diethyl ether (50 mL)
8. 8
   Filtrationthe insoluble material was collected by filtration
9. 9
   WaschenThe collected solid was washed with diethyl ether
10. 10
    Sonstigedried under reduced pressure

Vorschrift

To a solution of 2-(tert-butoxycarbonylamino)-2-methylpropionate (4.06 g) in N,N-dimethylformamide (40 mL) were added 1-(benzyloxycarbonyl)piperazine (6.6 g), 1-hydroxybenzotriazole (3.24 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (7.67 g) and triethylamine (11.2 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, 1 mol/L aqueous sodium hydroxide solution, water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added 4 mol/L hydrochloric acid (1,4-dioxane solution, 25 mL), and the mixture was stirred at room temperature for 4 hours. To the reaction mixture was added diethyl ether (50 mL), and the insoluble material was collected by filtration. The collected solid was washed with diethyl ether and dried under reduced pressure to give the title compound (4.65 g).

Quelle