Sodium Carbonate → HCID 57137967, compound

HRID 2227209Notes

Reaction equation

HRID 2227209 reaction equation
[Br:1][C:2]1[N:6]([C@@H:7]2[O:12][C@H:11]([CH3:13])[C@@:9](C(=O)C)([OH:10])[C@H:8]2[F:17])[C:5]2[CH:18]=[C:19]([Cl:23])[C:20]([Cl:22])=[CH:21][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.C(O)C.O>[Br:1][C:2]1[N:6]([C@@H:7]2[O:12][C@H:11]([CH3:13])[C@@H:9]([OH:10])[C@H:8]2[F:17])[C:5]2[CH:18]=[C:19]([Cl:23])[C:20]([Cl:22])=[CH:21][C:4]=2[N:3]=1

Participants

6

Reactant 2

HCID 10340Sodium CarbonateHCID 57070594HCID 57070594, compound

Product 1

HCID 57137967HCID 57137967, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2-Bromo-5,6-dichloro-1-(3-acetyl-2,5-dideoxy-2-fluoro-beta-D-ribofuranosyl)-1H-benzimidazole (0.42 g, 1.0 mmoles) was dissolved in methanol and ethanol (17 mL each). Sodium carbonate (0.22 g, 2.1 mmoles, 2 eq.) was dissolved in 4.2 mL water and added to the starting material solution. The reaction was stirred at room temperature overnight. The solution was diluted with water (40 mL). The product was extracted with ethyl acetate (2×). The ethyl acetate solution was dried with MgSO4, filtered, and the solvent removed in vacuo. The residue purified by chromatography on 75 g of silica gel eluted with ethyl acetate/hexane (1:4, v/v) followed by (1:2, v/v). The product containing fractions were combined and the solvents removed in vacuo. The yield was 0.3 g, 75%. MS (FAB(+): m/z, 383; 1H NMR (DMSO-d6) δ7.97 (s, 1H, Ar—H), 7.88 (s, 1H, Ar—H), 6.20 (d, 1H, H-1′, J=19 Hz), 5.77 (d, 1H, OH-3′, J=5 Hz), 5.40 (d, 1H, H-2′, J=53 Hz), 4.0 (m, 2H,), 1.40 (d, 3H, H-5′, J=6 Hz).

Workup

  1. additionadded to the starting material solution
  2. extractionThe product was extracted with ethyl acetate (2×)
  3. dry with materialThe ethyl acetate solution was dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue purified by chromatography on 75 g of silica gel
  7. washeluted with ethyl acetate/hexane (1:4, v/v)
  8. additionThe product containing fractions
  9. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-f35af746555149c6837166c7bf0ca385
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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