Methanol → 3,4-Dichloro-2-(isopropylamino)-1-(beta-L-ribofuranosyl)-1H-benzimidazole

HRID 1532611Notes

Reaction equation

HRID 1532611 reaction equation
[Cl:1][N:2]1[C:6]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C@H:12]2[O:24][C@@H:23]([CH2:25][O:26]C(=O)C)[C@H:18]([O:19]C(=O)C)[C@@H:13]2[O:14]C(=O)C)[CH:3]1[NH:30][CH:31]([CH3:33])[CH3:32].C(=O)([O-])[O-].[Na+].[Na+].O.CO>C(O)C>[Cl:1][N:2]1[C:6]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C@H:12]2[O:24][C@@H:23]([CH2:25][OH:26])[C@H:18]([OH:19])[C@@H:13]2[OH:14])[CH:3]1[NH:30][CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10340Sodium CarbonateHCID 572228243,4-Dichloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 572794253,4-Dichloro-2-(isopropylamino)-1-(beta-L-ribofuranosyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dichloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (2.06 g, 4.10 mmol), sodium carbonate (0.60 g, 5.66 mmol), water (12 mL), methanol (10 mL), and ethanol (24 mL) were used according to general procedure III. The product was purified by silica gel chromatography using 10:1 dichloromethane/methanol to afford a white solid.

Workup

  1. customThe product was purified by silica gel chromatography
  2. customto afford a white solid

Sources & evidence

ORD record
ord-552ca6e82ecd40d9a4b89350ee517797
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

Loading…