Reacción #944

ord-57d496f8cfa74e14b0b60ed9b08a5969

Ecuación de reacción

CCC(N)C(=O)O
2-aminobutyric acid
O=S(Cl)Cl
thionyl chloride
CCOCC
diethyl ether
CCOC(=O)C(N)CC.Cl
desired product
CCOC(=O)C(N)CC.Cl
Ethyl 2-aminobutyrate hydrochloride

Disolventes

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturagradually warmed to room temperature
  2. 2
    TemperaturaThe resulting white slurry was heated
  3. 3
    Temperaturaunder reflux for 3 hours
  4. 4
    workup.WAITleft
  5. 5
    Temperaturato cool for 10 minutes
  6. 6
    workup.ADDITIONpoured
  7. 7
    workup.STIRRINGwith hand stirring
  8. 8
    FiltraciónThe suspension was filtered
  9. 9
    Otrothe solid product dried

Procedimiento

A slurry of 2-aminobutyric acid (100 g, Aldrich) in absolute ethanol (300 ml) was stirred under nitrogen at 0° C. and thionyl chloride (120.8 g) was added dropwise. The reaction was stirred overnight at 0° C. and then gradually warmed to room temperature. The resulting white slurry was heated under reflux for 3 hours, left to cool for 10 minutes, then poured into chilled diethyl ether (600 ml), with hand stirring. The suspension was filtered and the solid product dried to give the desired product (150 g) as a white solid. 1H NMR consistent with proposed structure.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723458uspto-grants-1998_03