Carbon Dioxide → Methyl 4-(butylamino)-4-oxobutanoate

HRID 1905669Notes

Reaction equation

HRID 1905669 reaction equation
[CH2:1]([NH:5][C:6](=[O:12])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[C:18]([O-])(O)=O.[Na+].C(=O)=O>CO>[CH2:1]([NH:5][C:6](=[O:12])[CH2:7][CH2:8][C:9]([O:11][CH3:18])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 244664butanoic acid, 4-(butylamino)-4-oxo-HCID 516892Sodium Bicarbonate

Product 1

HCID 15207831Methyl 4-(butylamino)-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-butylamino-4-oxobutanoic acid (20 mmol) and concentrated sulfuric acid (1 ml) in MeOH (40 ml) is heated at reflux for 8 hours. The reaction is cooled to room temperature and saturated NaHCO3 is carefully added until CO2 gas no longer evolves. Most of the MeOH is removed in vacuo and the residue is partitioned between Et2O (100 ml) and H2O (40 ml). The water layer is re-extracted with Et2O (50 ml). The combined Et2O layers are washed with H2O (20 ml×2) and dried. Filtration and evaporation of solvent gives the title compound.

Workup

  1. temperatureat reflux for 8 hours
  2. customMost of the MeOH is removed in vacuo
  3. customthe residue is partitioned between Et2O (100 ml) and H2O (40 ml)
  4. extractionThe water layer is re-extracted with Et2O (50 ml)
  5. washThe combined Et2O layers are washed with H2O (20 ml×2)
  6. customdried
  7. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-473dc99d3e524741a9ab1a5245a0cad7
Source dataset
uspto-grants-1987_03
Patent number
US04647573

Reaction notes

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