Реакция #75531

Уравнение реакции

cystamine dihydrochloride

butyl chloroformate

triethylamine hydrochloride

triethylamine

HCl

Arachidonic acid

triethylamine

→

N,N′-diarachidonoylcystamine

Выход 75.0%

Растворители

methanol

acetonitrile

Условия реакции

Обработка

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

Методика

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.

Источник