Imidazole → N-(9-((2R,4S,5R)-5-((Tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-YL)-9H-purin-6-YL)benzamide

HRID 968368

Reaktionsgleichung

Reaktionsgleichung von HRID 968368
[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:23]=2[N:24]=[CH:25][N:26]=1)[C@@H:15]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>CN(C=O)C>[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:23]=2[N:24]=[CH:25][N:26]=1)[C@@H:15]1[O:22][C@H:19]([CH2:20][O:21][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C@@H:17]([OH:18])[CH2:16]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 107558N-benzoyl-2'-deoxyadenosine

Produkt 1

HCID 13833804N-(9-((2R,4S,5R)-5-((Tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-YL)-9H-purin-6-YL)benzamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

N6-benzoyl-2′-deoxyadenosine (20.95 g ) was dissolved in 200 ml of DMF. Imidazole (15.7 g) was dissolved to the resultant solution by addition. Then, 20.8 g of tert-butyldimethylsilyl chloride was added. DMF (100 ml) was further added and the solution was stirred at room temperature. After 8 hours, extraction using chloroform was carried out and the organic layer was washed by a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After concentration of the extract, the target compound was purified by column chromatography (methanol/chloroform) to obtain 16.1 g of the titled compound (yield; 61%).

Aufarbeitung

  1. extractionextraction
  2. washthe organic layer was washed by a saturated aqueous solution of sodium chloride
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customAfter concentration of the extract, the target compound was purified by column chromatography (methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-81469bcec1824a7484d68d38a907143f
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06958391B2

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