Lithium Hydroxide → HCID 54509299, compound

HRID 1281676Notes

Reaction equation

HRID 1281676 reaction equation
[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([O:19]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.[Li+].[OH-]>O1CCOCC1.P([O-])([O-])([O-])=O>[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([OH:19])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54506767HCID 54506767, compound

Product 1

HCID 54509299HCID 54509299, compound

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-5-chloro-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.15 g, 0.31 mmol) was deprotected as outlined in General Procedure V by being dissolved in 5 ml dioxane at rt. To this solution was added all at once, 1.2 ml (1.2 mmol) of 1M aq. LiOH. The mixture stirred at ambient temperature for 0.25 h. The mixture was diluted with 15 ml of pH 7 phosphate buffer and extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate (anhyd.), filtered and solvents evaporated. The residue was triturated in dichloromethane and 2-bromo-5-chloro-1-beta-D-ribopyranosyl-1H-benzimidazole was collected by vacuum filtration. The product was dried in a vacuum oven at 50° C. (0.041 g , 0.11 mmol 37%); m.p. 120° C. (foams), 150° C. (decomposes); 1H NMR (DMSO-d6) δ7.70-7.67 (m,2H), 7.24-7.22 (d, 1H, J=8.7 Hz), 5.64-5.61 (d, 1H,J=9.2 Hz), 5.16 (bs, 1H), 4.07-4.05 (overlapping dd, 1H), 3.98 (bs, 1H), 3.87-3.66 (m, 1H), 3.68-3.66 (d, 2H,J=8.5 Hz).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over magnesium sulfate (anhyd.)
  3. filtrationfiltered
  4. customsolvents evaporated
  5. customThe residue was triturated in dichloromethane
  6. filtration2-bromo-5-chloro-1-beta-D-ribopyranosyl-1H-benzimidazole was collected by vacuum filtration
  7. customThe product was dried in a vacuum oven at 50° C. (0.041 g , 0.11 mmol 37%)
  8. customm.p. 120° C. (foams), 150° C. (decomposes)

Sources & evidence

ORD record
ord-2b2ce9f78f874900b25e726d8e123332
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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