Sodium Acetate → Tert-butyl 5-(2-chloro-4-nitroimidazol-1-yl)-4-hydroxy-4-methylpentanoate

HRID 856171Notes

Reaction equation

HRID 856171 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][C:7]1([CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][O:8]1.[Cl:19][C:20]1[NH:21][CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[N:24]=1>C(O)C>[Cl:19][C:20]1[N:21]([CH2:9][C:7]([OH:8])([CH3:6])[CH2:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[N:24]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 23081086Tert-butyl 3-(2-methyl-2-oxiranyl)propionateHCID 178526855HCID 178526855, compound

Product 1

HCID 23081446Tert-butyl 5-(2-chloro-4-nitroimidazol-1-yl)-4-hydroxy-4-methylpentanoateYield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (0.59 g, 7.18 mmol) was added to a suspension of tert-butyl 3-(2-methyloxiran-2-yl)propionate (1.00 g, 5.39 mmol) and 2-chloro-4-nitro-1H-imidazole (0.53 g, 3.59 mmol) in ethanol (5 ml) followed by stirring under reflux for 6 hours. Insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl 5-(2-chloro-4-nitroimidazol-1-yl)-4-hydroxy-4-methylpentanoate (0.94 g, yield 78%) as a light yellow oil.

Workup

  1. temperatureunder reflux for 6 hours
  2. customInsoluble matters were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-6605f7dd34e04cc7b39fe125d43dcfe6
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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