Water → HCID 70874980, compound

HRID 2172263Notes

Reaction equation

HRID 2172263 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:35])([CH3:34])[CH2:23][CH2:24][N:25]3[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[N:27]=[C:26]3Cl)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3([CH3:34])[O:35][C:26]4=[N:27][C:28]([N+:30]([O-:32])=[O:31])=[CH:29][N:25]4[CH2:24][CH2:23]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 70873547HCID 70873547, compound

Product 1

HCID 70874980HCID 70874980, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{4-[4-(2-Chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylbutoxy]phenyl}piperazine-1-carboxylic acid tert-butyl ester (2.12 g) was dissolved in dimethylformamide (21 ml). 60% sodium hydride (0.24 g) was added thereto, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, the mixture was subjected to extraction with methylene chloride, and then dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:0→methylene chloride:ethyl acetate=1:1) to afford the title compound as a colorless powder (1.05 g).

Workup

  1. extractionthe mixture was subjected to extraction with methylene chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtering
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:0→methylene chloride:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9d1e0db7cec649769a40dee49cf15da9
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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