Acetic Acid → HCID 86592809, compound

HRID 1061501Notes

Reaction equation

HRID 1061501 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:33][C@H:32]([CH2:34][O:35]C(=O)C4C=CC=CC=4)[C@@H:22]([O:23]C(=O)C4C=CC=CC=4)[C@H:12]3[O:13]C(=O)C3C=CC=CC=3)[C:6]=2[C:5]([F:44])=[CH:4][N:3]=1.C[O-].[Na+].C(O)(=O)C>CO>[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:33][C@H:32]([CH2:34][OH:35])[C@@H:22]([OH:23])[C@H:12]3[OH:13])[C:6]=2[C:5]([F:44])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 15539668HCID 15539668, compound

Product 1

HCID 86592809HCID 86592809, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-chloro-7-fluoro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridine (45, 0.73 g, 1.2 mmol) in dry methanol (50 mL) was added sodium methoxide until pH 10 was reached. The reaction mixture was refluxed for 30 min, cooled, neutralized with glacial acetic acid, and evaporated to dryness. The residue was purified by silica gel column chromatography (CH2Cl2/EtOH, 10:1, v/v) to give 0.29 g (78%) as a white solid: mp 187-189° C.; 1H NMR (DMSO-d6) δ3.58 (m, 1 H, 5′-HA), 3.70 (m, 1 H, 5′-HB), 3.99 (m, 1 H, 4′-H), 4.13 (m, 1 H, 3′-H), 4.36 (m, 1 H, 2′-H), 5.16 (t, 1 H, 5′-OH, D2O exchangeable), 5.28 (d, 1 H, OH, D2O exchangeable), 5.63 (d, 1 H, OH, D2O exchangeable), 6.03 (d, 1 H, 1′-H, J=5.1 Hz), 8.27 (d, 1 H, 6-H, J=2.1 Hz), 8.88 (s, 1 H, 2-H). Analysis calculated for C11H11ClFN3O4: C, 43.50; H, 3.65; N, 13.84. Found: C, 43.43; H, 3.26; N, 13.81.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. temperaturecooled
  3. customevaporated to dryness
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2/EtOH, 10:1
  5. customv/v) to give 0.29 g (78%) as a white solid

Sources & evidence

ORD record
ord-3514a427696f4f8487cd865578481cd8
Source dataset
uspto-grants-2005_11
Patent number
US06960568B2

Reaction notes

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