Reaktion #75531

Reaktionsgleichung

cystamine dihydrochloride

butyl chloroformate

triethylamine hydrochloride

triethylamine

HCl

Arachidonic acid

triethylamine

→

N,N′-diarachidonoylcystamine

Ausbeute 75.0%

Lösungsmittel

methanol

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITwas continued for 15 min at −15° C.
2. 2
   Sonstigethe mixture obtained
3. 3
   Temperaturto warm to room temperature
4. 4
   workup.WAITAfter 2 h
5. 5
   Extraktionthe mixture was extracted with ether (20 ml)
6. 6
   WaschenThe extract was washed with water
7. 7
   Trocknendried with Na2SO4
8. 8
   Sonstigeevaporated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 2 ml of chloroform
10. 10
    Sonstigepurified by column (2×2 cm) chromatography on aluminium oxide (basic, Brockmann II)
11. 11
    WaschenElution of the column
12. 12
    Sonstigewith chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions

Vorschrift

Arachidonic acid (152 mg, 0.5 mmol) and triethylamine (52 mg, 0.51 mmol) were dissolved in 3 ml of dry acetonitrile and chilled to −15° C., and 70 mg (0.51 mmol) of butyl chloroformate was added. After 30 min, the mixture free of the precipitated triethylamine hydrochloride was pipetted in a solution of cystamine dihydrochloride (56 mg, 0.25 mmol) and triethylamine (52 mg, 0.51 mmol) in 1 ml of methanol, stirring was continued for 15 min at −15° C., then the mixture obtained was allowed to warm to room temperature. After 2 h, 0.5 M HCl was added, and the mixture was extracted with ether (20 ml). The extract was washed with water, then dried with Na2SO4, and evaporated under reduced pressure. The residue was dissolved in 2 ml of chloroform and purified by column (2×2 cm) chromatography on aluminium oxide (basic, Brockmann II). Elution of the column with chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions gave 181 mg (75%) of the desired N,N′-diarachidonoylcystamine as a waxy solid: TLC, Merck silica gel 60 pre-coated plates [system A: benzen-dioxan-acetic acid (25:5:1 v/v/v)] Rf0.5.

Quelle