Sodium Carbonate → HCID 70177971, compound

HRID 2227201Notes

Reaction equation

HRID 2227201 reaction equation
[Br:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH3:20])[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.CCO.O>[Br:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH3:20])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:4]=2[N:3]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 70177980HCID 70177980, compound

Product 1

HCID 70177971HCID 70177971, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.44 g (1 mmol) of 2-bromo-6-chloro-1-(2,3-di-O-acetyl-5-deoxy-β-D-ribofuranosyl)-1H-benzimidazole and 0.17 g (1.6 mmol) of sodium carbonate in 8 mL of MeOH, 8 mL of EtOH and 2 mL of water was stirred at room temperature for 6 h. The reaction mixture was concentrated and redissolved in 50 mL of EtOAc. After 2 washings with saturated brine, the EtOAc solution was dried over MgSO4. Solvent removal resulted in a crude product which was flash column chromatographed on silica gel with EtOAc/hexane (1:1) to give 0.24 g (69%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ1.4 (d, 3H, CH3), 3.8-3.9 (m, 1H, CH), 3.9-4 (m, 1H, CH), 4.45 (q, 1H, CH), 5.21 (d 1H, OH), 5.45 (d, 1H, OH), 5.8 (d, 1H, CH), 7.3 (d, 1H, aromatic), 7.6 (s,1H, aromatic), 7.62 (d, 1H, aromatic).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in 50 mL of EtOAc
  3. washAfter 2 washings with saturated brine
  4. dry with materialthe EtOAc solution was dried over MgSO4
  5. customSolvent removal
  6. customresulted in a crude product which
  7. customchromatographed on silica gel with EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-1c7b872a03264db38cbd584d9f8492ff
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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