Reaktion #529880

Reaktionsgleichung

chloroform methanol

adenine

potassium carbonate

rac-1,2-epoxy-3-octadecyloxypropane

→

9-[2'-hydroxy-3'-octadecyloxypropyl]-adenine

Ausbeute 32.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture is filtered directly
2. 2
   Temperaturwithout cooling
3. 3
   Einengenthe filtrate is concentrated in vacuo
4. 4
   Sonstigeto afford a white residue
5. 5
   FiltrationThe insoluble solid is filtered
6. 6
   Sonstigepurified by chromatography
7. 7
   Sonstigedried in vacuo

Vorschrift

A mixture of adenine (0.829 g, 6.10 mmol), anhydrous potassium carbonate (45 mg) and rac-1,2-epoxy-3-octadecyloxypropane (2.0 g, 6.13 mmol) in anhydrous dimethylformamide (10 mL) is stirred at 70°-75° C. for 20 hours under a nitrogen atmosphere. The reaction mixture is filtered directly without cooling, and the filtrate is concentrated in vacuo to afford a white residue. The residue is stirred with 95:5 (v/v) chloroform-methanol. The insoluble solid is filtered, purified by chromatography, and dried in vacuo to give 0.9 g (31.8%) of 9-[2'-hydroxy-3'-octadecyloxypropyl]-adenine (CPR 1148): Thin-layer Chromatography (TLC); 4×8 cm silica gel 60, 0.25 mm thickness, 10:2:0.2 (v/v/v) CHCl3 -CH3OH-30% aqueous ammonia (Rf value=0.65); mp 151°-152° C.

Quelle