反応 #86014

反応方程式

hydrochloric acid

ethyl 2-bromoacetate

diethyl 2-benzyloxycarbonylaminomalonate

sodium hydride

→

title compound

収率 87.3%

diethyl 2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinate

収率 87.3%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
2. 2
   workup.STIRRINGthe mixture was stirred overnight
3. 3
   抽出the mixture was extracted with ethyl acetate
4. 4
   洗浄the extract was washed with saturated brine
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   その他The solvent was evaporated under reduced pressure
7. 7
   洗浄the residue was subjected to silica gel column chromatography, in which elution
8. 8
   その他was performed with n-hexane/ethyl acetate (5:1) for purification
9. 9
   その他crystallized from ethyl acetate/n-hexane

実験手順

A solution of diethyl 2-benzyloxycarbonylaminomalonate (50 g) in anhydrous DMF (300 mL) was added portionwise with sodium hydride (60%, 6.47 g) with ice cooling and stirring, then the mixture was stirred at room temperature for 30 minutes, and subsequently added with ethyl 2-bromoacetate (22.6 g), and the mixture was stirred overnight. The reaction mixture was poured into diluted hydrochloric acid, the mixture was extracted with ethyl acetate, and 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 (5:1) for purification, and then crystallized from ethyl acetate/n-hexane to obtain the title compound (46.7 g, yield: 83%) as colorless crystals.

出典