Sodium Carbonate → HCID 54160475, compound

HRID 1281668Notes

Reaction equation

HRID 1281668 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]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>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]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 53919133HCID 53919133, compound

Product 1

HCID 54160475HCID 54160475, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An alcoholic solution of 2-bromo-5,6-dichloro-1-(2,3,4-tri-O-acetyl-beta-L-ribopyranosyl)-1H-benzimidazole (0.50 g, 0.95 mmol) was deprotected according to General Procedure VI with 0.61 g (5.8 mmol) of sodium carbonate in 5 ml of water. After stirring overnight at ambient temperature, the mixture was filtered and treated as described in General Procedure VI to give 2-bromo-5,6-dichloro-1-beta-L-ribopyranosyl-1H-benzimidazole (0.27 g, 0.68 mmol, 72% yield); MS (API+): m/z (rel. intensity) 398 (1.0, M+); 1H NMR (DMSO-d6) δ7.96 (s,1H), 7.07 (s, 1H), 5.64-5.62 (d, J=9.2 Hz), 5.19-5.17 (d, 1H, J=6.4 Hz), 5.13-5.12 (d, 1H, J=3.2 Hz), 4.86-4.84 (d, 1H, J=6.5 Hz), 4.12-4.06 (m, 1H), 3.98-3.92 (m, 2H), 3.68-3.63 (m, 2H).

Workup

  1. filtrationthe mixture was filtered
  2. additiontreated

Sources & evidence

ORD record
ord-618a2a777aa14c49885c91f34b9578ed
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

Loading…