反応 #86032

反応方程式

potassium carbonate

(R)-1-Benzyl ethyl 3-t-butyloxycarbonylamino-3-carbamoylsuccinate

hydrochloric acid

→

title compound

収率 90.0%

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

収率 90.0%

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)-1-Benzyl ethyl 3-t-butyloxycarbonylamino-3-carbamoylsuccinate (550 mg) obtained in Example 20 was dissolved in acetone (11 mL) and water (6 mL), the solution was added with potassium carbonate (231 mg), the mixture was stirred for 5 hours, and poured with 1 mol/L hydrochloric acid, 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 (358 mg, yield: 90%) as colorless crystals. Optical rotation [α]D25 was −29.5° (c 0.50, ethanol).

出典