Citric Acid → HCID 73013559, compound

HRID 1272099Notes

Reaction equation

HRID 1272099 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]2=[N:10][C:11]([Cl:15])=[C:12]([OH:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5].[H-].[Na+].[CH2:26](Br)[CH3:27].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:16]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C:9]2=[N:10][C:11]([Cl:15])=[C:12]([O:14][CH2:26][CH3:27])[CH:13]=[C:8]2[CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 73013560HCID 73013560, compound

Product 1

HCID 73013559HCID 73013559, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g (2.93 mmol) 6-chloro-5-hydroxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 20 mL N,N-dimethylformamide was added 0.14 g (3.23 mmol) sodium hydride (60% dispersion in mineral oil). After 30 min., 0.44 mL (0.64 g, 5.87 mmol) ethyl bromide was added and the suspension stirred for 1 h. The reaction mixture was poured into 10% aqueous citric acid solution and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:2) as eluant to give the product as a colourless crystalline solid (93.4%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:2) as eluant

Sources & evidence

ORD record
ord-8265714493184f47aa69d31308e9777e
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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