Sodium Carbonate → HCID 53822807, compound

HRID 1281700Notes

Reaction equation

HRID 1281700 reaction equation
[Br:1][C:2]1[N:6]([C@H:7]2[O:20][CH2:19][C@@H:14]([O:15]C(=O)C)[C@@H:9]([O:10]C(=O)C)[CH2:8]2)[C:5]2[CH:21]=[C:22]([Cl:26])[C:23]([Cl:25])=[CH:24][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:20][CH2:19][C@@H:14]([OH:15])[C@@H:9]([OH:10])[CH2:8]2)[C:5]2[CH:21]=[C:22]([Cl:26])[C:23]([Cl:25])=[CH:24][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 53745225HCID 53745225, compound

Product 1

HCID 53822807HCID 53822807, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ethanolic solution of 2-bromo-5,6-dichloro-1-(3,4-di-O-acetyl-2-deoxy-alpha-D-erythro-pentopyranosyl)-1H-benzimidazole (0.21 g, 0.45 mmol) was deprotected in a modification of General Procedure VI with 0.12 g (1.17 mmol) of sodium carbonate in 1 ml of water. After stirring overnight at ambient temperature, the mixture was treated as described in General Procedure VI. The crude product was triturated in ethyl acetate to give 0.11 g (0.29 mmol, 65% yield) of 2-bromo-5,6-dichloro-1-(2-deoxy-alpha-D-erythro-pentopyranosyl)-1H-benzimidazole. 1H NMR (DMSO-d6) δ8.15 (s, 1H), 7.96 (s, 1H), 5.80-5.77 (d, 1H), 5.12 (bs, 1H), 4.97 (m, 1H), 3.97-3.90 (m, 2H), 3.78-3.70 (m, 2H), 2.42-2.35 (m, 1H), 1.83-1.79 (m, 1H).

Workup

  1. additionthe mixture was treated
  2. customThe crude product was triturated in ethyl acetate

Sources & evidence

ORD record
ord-00cfe1149a54464db7b5d67f2df29ca0
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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