Ethyl 4-trichloroacetamido-5-hexenoate → Vigabatrin

HRID 1721741Notes

Reaction equation

HRID 1721741 reaction equation
ClC(Cl)(Cl)C([NH:5][CH:6]([CH:14]=[CH2:15])[CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])=O>Cl>[NH2:5][CH:6]([CH:14]=[CH2:15])[CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 11055787Ethyl 4-trichloroacetamido-5-hexenoate

Product 1

HCID 5665VigabatrinYield 139.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of ethyl 4-trichloroacetoamido-5-hexenoate (0.3 g, 1 mmol) in 6N HCl (10 mL) was heated under reflux 6 H. Then the mixture was concentrated in vacuo, diluted with water (10 mL), washed twice with Acoet, and dried in vacuo to give the title product (0.18 g, 100%). NMR, TLC (NH4OH:EtOH, 3:7) are identical with those of an authentic sample of 4-amino-5-hexenoic acid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux 6 H
  3. concentrationThen the mixture was concentrated in vacuo
  4. additiondiluted with water (10 mL)
  5. washwashed twice with Acoet
  6. customdried in vacuo

Sources & evidence

ORD record
ord-861ee6e14fbe4baa8f0923ff72427072
Source dataset
uspto-grants-1996_04
Patent number
US05512698

Reaction notes

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