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

HRID 2255943Notes

Reaction equation

HRID 2255943 reaction equation
[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

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2860092,5,6-Trichloro-1H-benzimidazoleHCID 12799408(3S,4R,5R)-2-chloro-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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 (Kieseigel 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)).

Workup

  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

Sources & evidence

ORD record
ord-d21aeb42414142189b1d0a3a7411d939
Source dataset
uspto-grants-1997_08
Patent number
US05654283

Reaction notes

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