반응 #76834

반응 방정식

(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

용매

acetonitrile

반응 조건

후처리

1. 1
   온도under reflux
2. 2
   기타After 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
   기타The organic phase was evaporated
6. 6
   기타purified by silica gel column chromatography

실험 절차

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.

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