Ethyl 4-trichloroacetamido-5-hexenoate → Vigabatrin

HRID 2259458Notes

Reaction equation

HRID 2259458 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 6H. 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-5hexenoic acid. 1H NMR (90 MHz) (D2), δ ppm. (TMS) 1.83 (m, 2H, CH2CO2), 2.33 (m, 2H, CH2CH2) 3.66 (m, 1H, CH--C=), 5.35 (m, 3H, CH2 =CH) .

Workup

  1. temperaturewas heated
  2. temperatureunder reflux 6H
  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-6e06c2072cde4946806148b362c69d0c
Source dataset
uspto-grants-1995_12
Patent number
US05473099

Reaction notes

Loading…