Sodium Carbonate → HCID 54026708, compound

HRID 1281704Notes

Reaction equation

HRID 1281704 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]([S:30][CH3:31])[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]([S:30][CH3:31])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 54473820HCID 54473820, compound

Product 1

HCID 54026708HCID 54026708, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ethanolic solution of 2-bromo-5-chloro-6-methylthio-1-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.047 g, 0.09 mmol) was deprotected in a modification of General Procedure VI with 0.036 g (0.34 mmol) of sodium carbonate in 0.5 ml of water. After stirring 1 h at ambient temperature, the mixture was treated as described in General Procedure VI. The product was dried overnight in vacuo to give 2-bromo-5-chloro-6-methylthio-1-beta-D-ribopyranosyl-1H-benzimidazole (0.035 g, 0.09 mmol, 98% yield). 1H NMR (DMSO-d6) δ7.73 (s, 1H), 7.37 (s, 1H), 5.63-5.60 (d, 1H), 5.16-5.14 (m, 2H), 4.91-4.89 (d, 1H), 4.00-3.99 (m, 2H), 3.86 (m, 1H), 3.71-3.68 (m, 2H), 2.52 (s, 3H).

Workup

  1. additionthe mixture was treated
  2. customThe product was dried overnight in vacuo

Sources & evidence

ORD record
ord-592a30ae8d60436188a8064518504fe7
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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