Reaktion #86018

Reaktionsgleichung

hydrochloric acid

(R)-diethyl 2-benzyloxycarbonylamino-2-carbamoylsuccinate

sodium ethoxide

→

title compound

Ausbeute 85.2%

(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

Ausbeute 85.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at the same temperature for 2 hours
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was recrystallized from ethyl acetate/n-hexane

Vorschrift

A solution of (R)-diethyl 2-benzyloxycarbonylamino-2-carbamoylsuccinate (200 mg) in dehydrated ethanol (10 mL) was added with sodium ethoxide (41 mg) with ice cooling and stirring, the mixture was stirred at the same temperature for 2 hours, then cold 1 mol/L hydrochloric acid was poured into the mixture, and the mixture was extracted with ethyl acetate. 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 recrystallized from ethyl acetate/n-hexane to obtain the title compound (149 mg, yield: 85%) as colorless crystals. Optical rotation [α]D28 was −31.8° (c 0.59, ethanol), and optical purity was 99.2% ee.

Quelle