2-Oxobutanoic Acid → 2-isovaleramidobut-2-enoic acid

HRID 1885840Notes

Reaction equation

HRID 1885840 reaction equation
O=[C:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[C:8]([NH2:14])(=[O:13])[CH2:9][CH:10]([CH3:12])[CH3:11].O>C1(C)C=CC=CC=1>[C:8]([NH:14]/[C:2](=[CH:6]\[CH3:7])/[C:3]([OH:5])=[O:4])(=[O:13])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 582-Oxobutanoic AcidHCID 962WaterHCID 10930Butanamide, 3-methyl-

Product 1

HCID 64438642-isovaleramidobut-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.07 g (10.5 mmole) of 2-ketobutyric acid and 0.71 g (7.0 mmole) of isovaleramide in 15 ml of toluene was stirred under reflux with collection of H2O in a small Dean-Stark trap. After 5 hrs, the solution was cooled, resulting in fairly heavy crystallization. After standing, the solid was collected on a filter and washed with toluene and then with CH2Cl2. Yield of white crystals=0.47 g, mp 172°-174° (slight prelim. softening). The material was recrystallized from diisopropyl ketone. Tlc (4:1 toluene-AcOH) now showed only a faint trace of the other isomer. Yield of white crystals=0.32 g (25%), mp 175° (slight prelim. softening). NMR indicated essentially exclusively Z-isomer.

Workup

  1. temperaturethe solution was cooled
  2. customresulting in fairly heavy crystallization
  3. customthe solid was collected on
  4. filtrationa filter
  5. washwashed with toluene
  6. customThe material was recrystallized from diisopropyl ketone

Sources & evidence

ORD record
ord-3f061978b2da4a568d3dddce56b357e3
Source dataset
uspto-grants-1992_09
Patent number
US05147868

Reaction notes

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