Sodium hydride → HCID 66664893, compound

HRID 1773527Notes

Reaction equation

HRID 1773527 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:11][C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1)=[O:6].CC1C=C(C)C=C(C)C=1S([NH:29]O)(=O)=O>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[N:11]([NH2:29])[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11009332O-mesitylenesulfonylhydroxylamineHCID 66664648HCID 66664648, compound

Product 1

HCID 66664893HCID 66664893, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% suspension in mineral oil, 90 mg) was added to a solution of 1H-pyrrole-2,5-dicarboxylic acid 2-ethyl ester 5-methyl ester (100 mg) in N,N-dimethylformamide (2 mL) and the resulting mixture was stirred for 5 minutes. 2,4,6-Trimethyl-benzenesulfonylhydroxylamine (prepared from 0.5 g of mesitilene oxamate as described in JOC 1973, 1239) was then added and the mixture was stirred for 5 minutes. The reaction mixture was then quenched by addition of water and the resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 90/10) to afford 100 mg of 1-amino-1H-pyrrole-2,5-dicarboxylic acid 2-ethyl ester 5-methyl ester.

Workup

  1. stirringthe mixture was stirred for 5 minutes
  2. customThe reaction mixture was then quenched by addition of water
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 90/10)

Sources & evidence

ORD record
ord-53e15f4e71604095bbf5cc85bde34f75
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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