Hexane → HCID 53822808, compound

HRID 1281701Notes

Reaction equation

HRID 1281701 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+].CCCCCC>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

5

Reactant 3

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 23383157HCID 23383157, compound

Product 1

HCID 53822808HCID 53822808, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ethanolic solution of 2-bromo-5,6-dichloro-1-(3,4-di-O-acetyl-2-deoxy-beta-D-erythro-pentopyranosyl)-1H-benzimidazole (0.13 g, 0.28 mmol) was deprotected in a modification of General Procedure VI with 0.077 g (0.73 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 dichloromethane and hexane to give 0.06 g (0.16 mmol, 56% yield) of 2-bromo-5,6-dichloro-1-(2-deoxy-beta-D-erythro-pentopyranosyl)-1H-benzimidazole. 1H NMR (DMSO-d6) δ8.01 (s, 1H), 7.92 (s, 1H), 5.96-5.94 (d, 1H), 5.02 (s, 1H), 4.90-4.89 (d, 1H), 4.01 (s, 1H), 3.94-3.86 (m, 1H), 3.74-3.72 (d, 2H), 2.42-2.39 (m, 1H—partially underneath residual DMSO signal), 1.90-1.87 (d, 1H).

Workup

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

Sources & evidence

ORD record
ord-21ad951dc089445aa0de0011e90b2f27
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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