Sodium hydride → N-(5-nitro-2-(pyrrol-1-yl)phenylmethyl)iminodicarboxylic acid di-tert-butyl ester

HRID 2227471

Reaction equation

HRID 2227471 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:9])([CH3:6])([CH3:5])[CH3:4].[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH:33]=[CH:32][CH:31]=[CH:30]2)=[C:25]([CH:28]=1)[CH2:26]Br)([O-:20])=[O:19]>CN(C)C=O>[C:14]([O:13][C:11]([N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:26][C:25]1[CH:28]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=[CH:23][C:24]=1[N:29]1[CH:33]=[CH:32][CH:31]=[CH:30]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 279800Di-tert-butyl IminodicarboxylateHCID 184740025-Nitro-2-(pyrrol-1-yl)benzyl bromide

Product 1

HCID 54574337N-(5-nitro-2-(pyrrol-1-yl)phenylmethyl)iminodicarboxylic acid di-tert-butyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of sodium hydride (60% content, 21 mg), iminodicarboxylic acid di-tert-butyl ester (117 mg) and dimethylformamide (5 ml), a solution in dimethylformamide (3 ml) of the compound (137 mg) obtained in Example 1c was added dropwise under cooling with ice. The reaction mixture was stirred for 2 hours at room temperature and then concentrated at reduced pressure. Brine was added to the resulting residue and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9) to give the titled compound (yield, 74%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationconcentrated at reduced pressure
  3. additionBrine was added to the resulting residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record
ord-19e89b8f35bd47a78da4095de7164f59
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Linked notes

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