Reaktion #1269838

ord-208da4c3a7d04dc4b4ededf4368c0617

Reaktionsgleichung

C=CC(=O)OCC
ethyl acrylate
CCOC(=O)CN.Cl
ethyl glycinate hydrochloride
[Na+].[OH-]
sodium hydroxide
CCOC(=O)CCNCC(=O)OCC
Diethyl-2-azabutane-1,4-dicarboxylate

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter 19 h the solution is partitioned with dichloromethane (3×100 mL)
  2. 2
    TrocknenThe organic layer is dried with anhydrous sodium sulfate
  3. 3
    Filtrationfiltered
  4. 4
    Sonstigeevaporated
  5. 5
    workup.DISTILLATIONThe residue is distilled
  6. 6
    Sonstigeto afford AA (28.8 g, 61%)

Vorschrift

A 4.7 M aqueous solution of sodium hydroxide (50 mL) is 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) is added and the mixture is stirred at room temperature until completion of the reaction is ascertained by TLC. After 19 h the solution is partitioned with dichloromethane (3×100 mL). The organic layer is dried with anhydrous sodium sulfate, filtered and evaporated. The residue is distilled to afford AA (28.8 g, 61%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08664193B2uspto-grants-2014_03