Acetic Acid → HCID 493368, compound

HRID 2109479Notes

Reaction equation

HRID 2109479 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Br:7][C:8]1[N:12]([C@H:13]2[O:25][C@@H:24]([CH2:26][O:27]C(=O)C)[C@H:19]([O:20]C(=O)C)[C@@H:14]2[O:15]C(=O)C)[C:11]2[CH:31]=[C:32]([Cl:36])[C:33]([Cl:35])=[CH:34][C:10]=2[N:9]=1.O.C(O)(=O)C>C(Cl)Cl.C(O)C.CO>[Br:7][C:8]1[N:12]([C@H:13]2[O:25][C@@H:24]([CH2:26][OH:27])[C@H:19]([OH:20])[C@@H:14]2[OH:15])[C:11]2[CH:31]=[C:32]([Cl:36])[C:33]([Cl:35])=[CH:34][C:10]=2[N:9]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 54518783HCID 54518783, compound

Product 1

HCID 493368HCID 493368, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium carbonate (0.28 g, 2.65 mmol) and 2-bromo-5,6-dichloro-1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1H-benzimidazole (1.39 g, 2.65 mmol) were combined with water (4 mL), methanol (20 mL) and ethanol (20 mL) and stirred at rt for 1.5 h. Acetic acid (0.3 mL, 5.3 mmol) was added and the suspension was concentrated to a solid. Purification of the residue on a silica gel column (2.5×20 cm, 230-400 mesh) with 1:9 ethanol:CH2Cl2 gave the title compound as a white amorphous solid (0.79 g, 2.0 mmol, 75%); m.p. 169° C.; [α]20D=(+)105 (c=0.5 DMF); UVλmax (E) pH=7.0: 298 nm (6,700), 289 (6,500), 255 (6,900); 0.1 nNaOH: 298 nm (6,700), 295 (5,400), 256 (6,700); MS (CI): m/z 399 (M+); 1H NMR (DMSO-d6) d 8.57 (s, 1H, Ar—H), 7.96 (s, 1H, Ar—H), 5.89 (d, J=7.9 Hz, H-1′), 5.48 (d, 1H, OH, J=6.3 Hz), 5.42 (t, 1H, OH, J=4.5 Hz), 5.29 (d, 1H, OH, J=4.2 Hz), 4.43 (apparent dd, 1H, H-2′, J=13.3 Hz, J=6.1 Hz), 4.14 (apparent t, 1H, H-3′, J=4.3 Hz), 4.01 (apparent d, 1H, H-4′, J=1.7 Hz), 3.77-3.63 (m, 2H, H-5′).

Workup

  1. concentrationthe suspension was concentrated to a solid
  2. customPurification of the residue on a silica gel column (2.5×20 cm, 230-400 mesh) with 1:9 ethanol

Sources & evidence

ORD record
ord-ddad2fd983a9492c8ea69671c925b2e7
Source dataset
uspto-grants-2009_04
Patent number
US07514568B2

Reaction notes

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