反応 #75531

反応方程式

cystamine dihydrochloride

butyl chloroformate

triethylamine hydrochloride

triethylamine

HCl

Arachidonic acid

triethylamine

→

N,N′-diarachidonoylcystamine

収率 75.0%

溶媒

methanol

acetonitrile

反応条件

後処理

1. 1
   workup.WAITwas continued for 15 min at −15° C.
2. 2
   その他the mixture obtained
3. 3
   温度to warm to room temperature
4. 4
   workup.WAITAfter 2 h
5. 5
   抽出the mixture was extracted with ether (20 ml)
6. 6
   洗浄The extract was washed with water
7. 7
   乾燥dried with Na2SO4
8. 8
   その他evaporated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 2 ml of chloroform
10. 10
    その他purified by column (2×2 cm) chromatography on aluminium oxide (basic, Brockmann II)
11. 11
    洗浄Elution of the column
12. 12
    その他with chloroform-methanol (9:1 v/v) and evaporation of the appropriate fractions

実験手順

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.

出典