Bromoacetic Acid → N-Isobutylglycine

HRID 396113Notes

Reaction equation

HRID 396113 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].Br[CH2:7][C:8]([OH:10])=[O:9]>>[CH2:1]([NH:5][CH2:7][C:8]([OH:10])=[O:9])[CH:2]([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 6227Bromoacetic AcidHCID 6558Isobutylamine

Product 1

HCID 10261121N-Isobutylglycine

Procedure

Isobutylamine (50 mL, 0.5 mol) was cooled in an ice bath, and bromoacetic acid (6.1 g, 43.9 mmol) added slowly as a solid, insuring that each piece dissolved. After stirring overnight, the excess amine was removed and MeOH was added to the resulting oil. The resulting mixture was concentrated, and repeated using MeOH/HCl. Finally, a white solid was recrystallized from ethanol/ether to provide N-isobutylglycine.HCl (3.95 g, 53.7%).

Workup

  1. dissolutiondissolved
  2. customthe excess amine was removed
  3. additionMeOH was added to the resulting oil
  4. concentrationThe resulting mixture was concentrated
  5. customFinally, a white solid was recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-4dfbaccf9c9c4ca7ab9d96c093f84925
Source dataset
uspto-grants-2003_08
Patent number
US06608026B1

Reaction notes

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