Reacción #86018

Ecuación de reacción

hydrochloric acid

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

sodium ethoxide

→

title compound

Rendimiento 85.2%

(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide

Rendimiento 85.2%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente