Reacción #577256

ord-b48a4b875f5f4f4ca1ffed6b3414a4b0

Ecuación de reacción

C=CC(=O)OCC
ethyl acrylate
CCOC(=O)CN.Cl
ethyl glycinate hydrochloride
[Na+].[OH-]
sodium hydroxide
CCOC(=O)CCNCC(=O)OCC
Diethyl2-azabutane-1,4-dicarboxylate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas ascertained by TLC (19 h)
  2. 2
    OtroAfter 19 h which it was partitioned with dichloromethane (3×100 mL)
  3. 3
    SecadoThe organic layer was dried with anhydrous sodium sulfate
  4. 4
    Filtraciónfiltered
  5. 5
    Otroevaporated
  6. 6
    workup.DISTILLATIONThe residue was distilled
  7. 7
    Otroto afford AA (28.8 g, 61%)

Procedimiento

A 4.7 M aqueous solution of sodium hydroxide (50 mL) was added into a stirred, ice-cooled solution of ethyl glycinate hydrochloride (32.19 g, 0.23 mole) in water (50 mL). Then, ethyl acrylate (23.1 g, 0.23 mole) was added and the mixture was stirred at room temperature until the completion of reaction was ascertained by TLC (19 h). After 19 h which it was partitioned with dichloromethane (3×100 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and evaporated. The residue was distilled to afford AA (28.8 g, 61%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07528118B2uspto-grants-2009_05