Reaktion #86014

Reaktionsgleichung

hydrochloric acid

ethyl 2-bromoacetate

diethyl 2-benzyloxycarbonylaminomalonate

sodium hydride

→

title compound

Ausbeute 87.3%

diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate

Ausbeute 87.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
2. 2
   workup.STIRRINGthe mixture was stirred overnight
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   Waschenthe extract was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Waschenthe residue was subjected to silica gel column chromatography, in which elution
8. 8
   Sonstigewas performed with n-hexane/ethyl acetate (5:1) for purification
9. 9
   Sonstigecrystallized from ethyl acetate/n-hexane

Vorschrift

A solution of diethyl 2-benzyloxycarbonylaminomalonate (50 g) in anhydrous DMF (300 mL) was added portionwise with sodium hydride (60%, 6.47 g) with ice cooling and stirring, then the mixture was stirred at room temperature for 30 minutes, and subsequently added with ethyl 2-bromoacetate (22.6 g), and the mixture was stirred overnight. The reaction mixture was poured into diluted hydrochloric acid, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, in which elution was performed with n-hexane/ethyl acetate (5:1) for purification, and then crystallized from ethyl acetate/n-hexane to obtain the title compound (46.7 g, yield: 83%) as colorless crystals.

Quelle