Reaktion #53238

Reaktionsgleichung

triethylamine

1,10-decanedicarboxylic acid

1-hydroxybenzotriazole

N,N-dimethylformamide

hydrochloride

→

decane-1,10-dicarboxamide

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at −5 degree C
2. 2
   workup.ADDITIONwere added
3. 3
   workup.STIRRINGstirred for 24 hours
4. 4
   Sonstigewhile gradually returning to room temperature
5. 5
   workup.DISTILLATIONThe solvent was completely distilled off under reduced pressure
6. 6
   Sonstigethe white precipitate obtained
7. 7
   Waschenwas washed
8. 8
   Filtrationon filter paper successively with 50 ml of 10 wt % citric acid aqueous solution, 20 ml water, 50 ml of 4 wt % sodium bicarbonate aqueous solution and 20 ml water

Vorschrift

0.46 g (2 mmol) of 1,10-decanedicarboxylic acid and 0.674 g (4.4 mol) of 1-hydroxybenzotriazole were dissolved in N,N-dimethylformamide, and 10 ml of a dichloromethane solution containing 0.90 g (4.4 mmol) of 1-ethyl-3-(3-dimethylaminopropyl) carboimido hydrochloride was added at −5 degree C. with stirring. After 1 hour, 10 ml of dichloromethane solution containing 1.51 g (4.4 mmol) of the above L-valyl-L-valinebenzylester hydrochloride followed by 0.62 ml (4.4 mmol) of triethylamine were added, and stirred for 24 hours while gradually returning to room temperature. The solvent was completely distilled off under reduced pressure, and the white precipitate obtained was washed on filter paper successively with 50 ml of 10 wt % citric acid aqueous solution, 20 ml water, 50 ml of 4 wt % sodium bicarbonate aqueous solution and 20 ml water. 0.98 g of N,N′-bis (L-valyl-L-valinebenzylester) decane-1,10-dicarboxamide was obtained as a white solid (yield 0.61%). 0.5 g (0.62 mmol) of this compound was dissolved in 100 ml dimethylformamide, 0.25 g of 10 wt % palladium/carbon was added as a catalyst, and catalytic hydrogenation was performed. After 6 hours, the catalyst was filtered off using cerite, and the solvent was distilled off under reduced pressure to obtain a colorless oil. The oil obtained was crystallized using a water-ethanol mixed solvent to give a white solid. After analysis, this white solid was N,N′-bis (L-valyl-L-valine) decane-1,10-dicarboxamide (corresponds to m=2, n=10 in general formula (1)).

Quelle