Pyridine → Ethyl 3-acetamido-2-oxopentanoate

HRID 7536

Reaction equation

HRID 7536 reaction equation
[C:1]([NH:4][CH:5]([CH2:9][CH3:10])[C:6]([OH:8])=O)(=[O:3])[CH3:2].N1C=CC=CC=1.ClC(=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>O1CCCC1>[C:1]([NH:4][CH:5]([CH2:9][CH3:10])[C:6](=[O:8])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 3061072-(Acetylamino)butanoic acid

Product 1

HCID 21935058Ethyl 3-acetamido-2-oxopentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.2 g (63.4 mmol) 2-(acetylamino)butanoic acid are suspended in 120 ml tetrahydro-furane and heated to reflux together with 15.0 g (190 mmol) pyridine and a bit of N,N-dimethylaminopyridine. While heating at reflux, 17.3 g (127 mmol) ethyl chloro(oxo)acetate are added dropwise. The reaction mixture is heated at reflux until no more evolution of gas can be observed. After cooling down to room temperature, the reaction mixture is added to ice water and the organic phase extracted with ethyl acetate. The dried organic phase is evaporated to dryness in vacuo, dissolved in ethanol and the solution directly used for the next reaction.

Workup

  1. temperatureheated
  2. temperatureWhile heating
  3. temperatureat reflux
  4. temperatureThe reaction mixture is heated
  5. temperatureat reflux until no more evolution of gas
  6. extractionthe organic phase extracted with ethyl acetate
  7. customThe dried organic phase is evaporated to dryness in vacuo
  8. dissolutiondissolved in ethanol
  9. customthe solution directly used for the next reaction

Sources & evidence

ORD record
ord-104f1562f4d446dfad9da36770411e4b
Source dataset
uspto-grants-2006_08
Patent number
US07087605B2

Linked notes

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