반응 #86027

반응 방정식

potassium carbonate

(R)-diethyl 2-t-butyloxycarbonylamino-2-carbamoylsuccinate

hydrochloric acid

→

title compound

수율 88.5%

(R)-2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinimide

수율 88.5%

용매

water

acetone

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   세척The extract was washed with saturated brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타The solvent was evaporated under reduced pressure
5. 5
   세척the residue was subjected to silica gel column chromatography, in which elution
6. 6
   기타was performed with n-hexane/ethyl acetate (1:1) for purification
7. 7
   기타recrystallized from ethyl acetate/n-hexane

실험 절차

(R)-diethyl 2-t-butyloxycarbonylamino-2-carbamoylsuccinate (590 mg) obtained in Example 15 was dissolved in acetone (6 mL) and water (6 mL), the solution was added with potassium carbonate (295 mg), the mixture was stirred for 6 hours, 1 mol/L hydrochloric acid was poured to 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 subjected to silica gel column chromatography, in which elution was performed with n-hexane/ethyl acetate (1:1) for purification, and then recrystallized from ethyl acetate/n-hexane to obtain the title compound (450 mg, yield: 88%) as colorless crystals. Optical rotation [α]D25 was −39.1° (c 0.50, ethanol).

출처