Lithium Hydroxide → HCID 53870175, compound

HRID 1281680Notes

Reaction equation

HRID 1281680 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]([F:30])[C:27]([F:29])=[CH:28][C:4]=2[N:3]=1.[Li+].[OH-]>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]([F:30])[C:27]([F:29])=[CH:28][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54109777HCID 54109777, compound

Product 1

HCID 53870175HCID 53870175, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-5,6-difluoro-1-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.88 g, 1.8 mmol), 20 ml dioxane and 7 ml (7 mmol) of 1 M aqueous LiOH was used to prepare 2-bromo-5,6-difluoro-1-beta-D-ribopyranosyl-1H-benzimidazole (0.23 g, 0.63 mmol, 35% yield) according to General Procedure V; MS (ES+): m/z (rel. intensity) 388 (1.0, M+23 (Na)); 1H NMR (DMSO-d6) δ7.83-7.79 (m, 1H), 7.73-7.68 (m, 1H), 5.62-5.60 (d, 1H, J=9.4 Hz), 4.10-4.08 (d, 1H, J=9.4 Hz), 3.97-3.95 (bs, 2H) 3.67-3.65 (d, 2H, J=8.2 Hz).

Sources & evidence

ORD record
ord-4b3cb676ae764e6e84762ec4b27b5660
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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