2-Chloro-5,6-dibromo-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole → (2R,3R,4S,5R)-2-(5,6-dibromo-2-chloro-benzimidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

HRID 263876Notes

Reaction equation

HRID 263876 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]=[C:26]([Br:30])[C:27]([Br:29])=[CH:28][C:4]=2[N:3]=1>N.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]=[C:26]([Br:30])[C:27]([Br:29])=[CH:28][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 105550222-Chloro-5,6-dibromo-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole

Product 1

HCID 469424(2R,3R,4S,5R)-2-(5,6-dibromo-2-chloro-benzimidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

A solution of 569 mg (1 mmole) of (56) in 20 mL of NH3 /MeOH was stirred in a sealed flask at room temperature for 5 hr. Volatile materials were removed by evaporation. The residue was recrystallized from MeOH to give 337 mg (2 crops, 76%) of 57. Its 1H NMR spectrum was identical to that of (57) prepared by a direct bromination; see Method B.

Workup

  1. customVolatile materials were removed by evaporation
  2. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-9fa5f66062d747f58c60f68d7721102a
Source dataset
uspto-grants-1997_07
Patent number
US05646125

Reaction notes

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