Citric Acid → HCID 67547587, compound

HRID 2356720Notes

Reaction equation

HRID 2356720 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]([NH:12][CH2:13][C:14]([C:16]3[CH:17]=[C:18]([Cl:21])[S:19][CH:20]=3)=[O:15])=[O:11])[CH:8]=[CH:9][C:2]1=2.[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]([NH:12][CH:13]([C:14]([C:16]3[CH:17]=[C:18]([Cl:21])[S:19][CH:20]=3)=[O:15])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:11])[CH:8]=[CH:9][C:2]1=2

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 59384489HCID 59384489, compound

Product 1

HCID 67547587HCID 67547587, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(5-benzo[b]furoyl)aminoacetyl]-2-chlorothiophene (543 mg) in N,N-dimethylformamide (10 ml) was added sodium hydride (71.3 mg, 60% mineral oil) under ice-cooling, and the mixture was stirred at room temperature for 20 minutes. After ice-cooling, ethyl bromoacetate (0.21 ml) was added dropwise to the mixture, and the resulting mixture was stirred at room temperature for 40 minutes. After cooling, 5% aqueous citric acid solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to obtain a crude product of ethyl 3-[(5-benzo[b]furoyl)amino]-4-(5-chlorothiophen-3-yl)-4-oxobutyrate (896 mg).

Workup

  1. temperaturecooling
  2. temperatureAfter ice-cooling
  3. stirringthe resulting mixture was stirred at room temperature for 40 minutes
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-84391fc9ce9c4e919c5222c3362e1051
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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