Reaktion #63849

Reaktionsgleichung

hydrochloric acid

glycine

(E,E)-4-ethyl-2,4-hexadienoic acid

N-hydroxysuccinimide

dicyclohexylcarbodiimide

→

N-[(E,E)-4-ethyl-2,4-hexadienoyl]glycine

Ausbeute 43.7%

Lösungsmittel

tetrahydrofuran

water

triethylamine

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   EinengenThe filtrate was concentrated to dryness under reduced pressure
3. 3
   Sonstigeto give a residue which
4. 4
   workup.STIRRINGThe resulting mixture was stirred at ambient temperature for 5 hours
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   WaschenThe extract was washed with water
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Einengenconcentrated to dryness under reduced pressure
9. 9
   Sonstigeto give a crystalline residue
10. 10
    SonstigeThe residue was triturated with a mixture of chloroform and hexane

Vorschrift

To a solution of (E,E)-4-ethyl-2,4-hexadienoic acid (2.8 g) and N-hydroxysuccinimide (2.3 g) in dioxane (20 ml) was added dicyclohexylcarbodiimide (4.32 g). The mixture was stirred at ambient temperature overnight and then filtered. The filtrate was concentrated to dryness under reduced pressure to give a residue which was dissolved in tetrahydrofuran (100 ml). To the solution was added a solution of glycine (4.5 g) and triethylamine (8.34 ml) in water (60 ml). The resulting mixture was stirred at ambient temperature for 5 hours, acidified with 1N hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure to give a crystalline residue. The residue was triturated with a mixture of chloroform and hexane to give N-[(E,E)-4-ethyl-2,4-hexadienoyl]glycine (1.72 g).

Quelle