Bromoacetic Acid → N-Isobutylglycine

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

Reactant 2

HCID 6227Bromoacetic Acid

HCID 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

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

Sources & evidence

ORD record: ord-ebc41319e76649ef90442a2e3702c9e1
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094758B2

Reaction notes

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