Sodium hydride → 2,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)benzimidazole

HRID 263890

Reaktionsgleichung

Reaktionsgleichung von HRID 263890
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[CH2:15]([O:22][C@H:23]1[C@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:26]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:25][CH:24]1Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC#N>[Cl:1][C:2]1[N:3]([C@@H:24]2[O:25][C@H:26]([CH2:36][O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:27]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@@H:23]2[O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2860092,5,6-Trichloro-1H-benzimidazoleHCID 127994081-chloro-Tri-2,3,5-O-benzyl-D-arabofuranose

Produkt 1

HCID 539929402,5,6-Trichloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)benzimidazoleAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Compound 5 (598 mg 2.7 mmole) was dissolved in dry CH3CN(60 ml) and 97% NaH (80 mg, 3 mmole) was added. The mixture was stirred under N2 for 1 hour at room temperature. Then 2,3,5-tri-O-benzyl-D-arabinofuranosyl chloride (prepared from 2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose) (1.83 g, 3 mmole)) dissolved in dry CH3CN (20 ml) was added dropwise. The mixture was stirred under N2 for overnight at room temperature. The reaction solution was filtered through Celite. The filtrate was evaporated to give a syrup and this syrup was subjected to flash column chromatography on silica gel (Kieselgel 60, 230-400 mesh) and eluted with CH2Cl2. The fractions containing 133 were combined and evaporated to give 1.6 g (95.0%) of 133. (IR KBr cm-1 : 1140-1060 (C--O--C)).

Aufarbeitung

  1. additionwas added dropwise
  2. stirringThe mixture was stirred under N2 for overnight at room temperature
  3. filtrationThe reaction solution was filtered through Celite
  4. customThe filtrate was evaporated
  5. customto give a syrup
  6. washeluted with CH2Cl2
  7. additionThe fractions containing 133
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ae85ec8d6d95409c851a5eb9f748bfd7
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646125

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