Water → HCID 86593206, compound

HRID 2356756Notes

Reaction equation

HRID 2356756 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:7](=[O:12])[CH2:8][NH:9][CH:10]=[O:11])=[CH:5][CH:6]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[S:3][C:4]([C:7](=[O:12])[CH:8]([NH:9][CH:10]=[O:11])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 86593204HCID 86593204, compound

Product 1

HCID 86593206HCID 86593206, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-5-(formylaminoacetyl)thiophene (20.1 g) in N,N-dimethylformamide (400 ml) was added sodium hydride (4.44 g, 60% mineral oil) under ice-cooling, and the mixture was stirred under argon atmosphere at room temperature for one hour. After ice-cooling, to the mixture was added dropwise ethyl bromoacetate (20.8 g), and the mixture was stirred at room temperature for 2 hours. After cooling, ice was added to the reaction mixture, and then water and ethyl acetate were also added to the mixture. The organic layer was collected washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=6:1) to obtain ethyl 4-(5-chlorothiophen-2-yl)-3-formylamino-4-oxobutyrate (17.8 g) as yellowish oil.

Workup

  1. temperaturecooling
  2. temperatureAfter ice-cooling, to the mixture
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. temperatureAfter cooling
  5. additionice was added to the reaction mixture
  6. customThe organic layer was collected
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-a795eba92414468ab5b9d6109a64ff66
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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