2-Chloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole → 22423-42-3

HRID 1985815Notes

Reaction equation

HRID 1985815 reaction equation
[Cl:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1.C[O-].[Na+].CO>CO>[Cl:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 218173932-Chloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazoleHCID 23694274Sodium methanolate methanol

Product 1

HCID 46942222423-42-3Yield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-benzimidazole (12.3 g) was dissolved in methanol (150 mL). To the mixture was added 28% sodium methoxide-methanol solution (1 mL), and the mixture was stirred for 1 hour. The reaction mixture was concentrated under reduced pressure to give the title compound (8.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4ef16211375a4b3f95d3e6dc4a1f36cd
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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