Acetic Acid → HCID 493368, compound

HRID 381641Notes

Reaction equation

HRID 381641 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-beta-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 2-bromo-5,6-dichloro-1-beta-L-ribofuranosyl-1H-benzimidazole as a white amorphous solid (0.79 g, 2.0 mmol, 75%); m.p. 169° C.; [a]20D=(+) 105 (c=0.5 DMF); UV 1max (e): pH 7.0: 298 nm (6,700), 289 (6,500), 255 (6,900); 0.1 N NaOH: 298 nm (6,700), 295 (5,400), 256 (6,700); MS (CI): m/z 399 (M+1); 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-ae75ba1147ec4645a7f502010f94f359
Source dataset
uspto-grants-2001_10
Patent number
US06307043B1

Reaction notes

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