反応 #86027

反応方程式

potassium carbonate

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

hydrochloric acid

→

title compound

収率 88.5%

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

収率 88.5%

溶媒

water

acetone

反応条件

後処理

1. 1
   抽出the mixture was extracted with ethyl acetate
2. 2
   洗浄The extract was washed with saturated brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他The solvent was evaporated under reduced pressure
5. 5
   洗浄the residue was subjected to silica gel column chromatography, in which elution
6. 6
   その他was performed with n-hexane/ethyl acetate (1:1) for purification
7. 7
   その他recrystallized from ethyl acetate/n-hexane

実験手順

(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).

出典