Reaktion #323693

Reaktionsgleichung

triethylamine

dibenzyl N-(L-threonyl)-L-glutamate

3-hexadecanoyloxyoctadecanoic acid

triethylamine

ethyl chloroformate

→

dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-glutamate

Ausbeute 81.5%

Lösungsmittel

ethyl acetate

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 1 hour at the same temperature
2. 2
   SonstigeTetrahydrofuran was removed under reduced pressure
3. 3
   Sonstigeto give the residue which
4. 4
   WaschenThe ethyl acetate solution was washed with diluted hydrochloric acid and diluted sodium bicarbonate
5. 5
   Sonstigedried
6. 6
   SonstigeEvaporation of the solvent
7. 7
   Sonstigegave the residue which
8. 8
   Sonstigewas recrystallized from ethanol

Vorschrift

To a solution of 3-hexadecanoyloxyoctadecanoic acid (55 g) and triethylamine (16 ml) in tetrahydrofuran (500 ml) was added ethyl chloroformate (11 ml) dropwise with stirring at -20° C., and the mixture was stirred for 1 hour at the same temperature. To the mixture was added triethylamine (32 ml) and then, a solution of dibenzyl N-(L-threonyl)-L-glutamate (77 g) in tetrahydrofuran (100 ml) dropwise and the mixture was stirred for 3 hours at room temperature. Tetrahydrofuran was removed under reduced pressure to give the residue which was taken up in ethyl acetate. The ethyl acetate solution was washed with diluted hydrochloric acid and diluted sodium bicarbonate and dried. Evaporation of the solvent gave the residue which was recrystallized from ethanol to leave dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-glutamate (79 g).

Quelle