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

HRID 1719173Notes

Reaction equation

HRID 1719173 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-b595770a00e94d83a672235b25ba5fbb
Source dataset
uspto-grants-1985_09
Patent number
US04539208

Reaction notes

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