Reaktion #76834

Reaktionsgleichung

(R)-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)guanine

N,N-diethylaniline

phosphorous oxychloride

→

(R)-2-Amino-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)-6-chloropurine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux
2. 2
   SonstigeAfter 3 hours the reaction mixture was evaporated in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane
4. 4
   workup.ADDITIONpoured into cold sodium hydrogen carbonate aqueous solution
5. 5
   SonstigeThe organic phase was evaporated
6. 6
   Sonstigepurified by silica gel column chromatography

Vorschrift

To a solution of (R)-9-(2-stearoyloxymethyl-4-(N-tert-butoxycarbonyl-L-valyloxy)butyl)guanine from step 2 of Example 1 (646 mg, 0.9 mmole) in acetonitrile were added tetramethylammonium chloride (427 mg, 2.7 mmole), N,N-diethylaniline (0.716 ml, 4.5 mmole) and phosphorous oxychloride (0.417 ml, 4.5 mmole). The reaction was kept under reflux and the progression monitored by TLC. After 3 hours the reaction mixture was evaporated in vacuo and the residue was dissolved in dichloromethane, then poured into cold sodium hydrogen carbonate aqueous solution. The organic phase was evaporated and purified by silica gel column chromatography. Yield: 251 mg.

Quelle