Lithium Hydroxide → HCID 54429635, compound

HRID 1281673Notes

Reaction equation

HRID 1281673 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]=[C:26]([CH3:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.[Li+].[OH-].BrC1N([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)C2C=C(Cl)C(Cl)=CC=2N=1>O1CCOCC1>[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]=[C:26]([CH3:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 30063172-Bromo-5,6-dichloro-1-β-D-ribopyranosyl-1H-benzimidazoleHCID 53855313HCID 53855313, compound

Product 1

HCID 54429635HCID 54429635, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-5-chloro-6-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.097 g ) was deprotected as outlined in General Procedure V by being dissolved in 5 ml dioxane and the resultant solution cooled in an ice bath between 0 and 5° C. To this solution was added all at once, 0.78 ml (0.78 mmol) of 1M aq. LiOH. The mixture was removed from the ice bath and allowed to stir at ambient temperature for 0.5 h. The mixture was diluted with 50 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 0.028 g (0.074 mmol) of 2-bromo-5,6-dichloro-1-beta-D-ribopyranosyl-1H-benzimidazole was collected by vacuum filtration. The product was dried in a vacuum oven at 50° C. overnight; m.p. 150° C. (foams); MS (AP+): m/z (rel. intensity) 400 (1.0, M+23 (Na)); 1H NMR (DMSO-d6) δ7.67 (s,1H), 7.65 (s, 1H), 5.62-5.60 (d, J=8.9 Hz), 5.13 (bs, 2H), 4.88-4.87 (m, 1H), 4.13 (bs, 1H), 4.00 (bs, 2H), 3.93 (m, 1H), 2.40 (s, 3H).

Workup

  1. customThe mixture was removed from the ice bath
  2. additionThe mixture was diluted with 50 ml of pH 7 phosphate buffer
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over magnesium sulfate (anhyd.)
  5. filtrationfiltered
  6. customsolvents evaporated
  7. customThe residue was triturated in dichloromethane
  8. customThe product was dried in a vacuum oven at 50° C. overnight

Sources & evidence

ORD record
ord-47b9bd75412440e3b5d89272ad137f15
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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