Reaktion #529881

Reaktionsgleichung

rac-1,2-Epoxy-3-octadecyloxypropane

cytosine

potassium carbonate

chloroform

→

1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosine

Ausbeute 37.3%

Lösungsmittel

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated in vacuo
2. 2
   Sonstigeto leave a residue
3. 3
   FiltrationThe undissolved material is filtered in vacuo
4. 4
   Einengenthe filtrate is concentrated in vacuo
5. 5
   Sonstigepurified by chromatography
6. 6
   Sonstigedried in vacuo

Vorschrift

rac-1,2-Epoxy-3-octadecyloxypropane (2.0 g, 6.13 mmol) is added to a mixture of cytosine (1.0 g, 9.0 mmol) and anhydrous potassium carbonate (40 mg) in dimethyl formamide (25 mL) over a 30 minute period under a nitrogen atmosphere. The resultant mixture is stirred at 80°-90° C. (oil bath temperature) for 48 hours. The reaction mixture is cooled to room temperature and concentrated in vacuo to leave a residue. The residue is stirred with chloroform (50 mL). The undissolved material is filtered in vacuo, and the filtrate is concentrated in vacuo, purified by chromatography and dried in vacuo to afford 1.0 g (37%) of 1-[2'-hydroxy-3'-octadecyloxypropyl]-cytosine (CPR 1149): 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=0.66); mp 153°-154° C.

Quelle