反应 #1375812

反应方程式

sodium bicarbonate

sodium hydride

N-benzyl-2-(4-hydroxybenzyl)-3-azaglutaric acid-di-tert-butyl ester

ethyl iodide

→

N-Benzyl-2-(4-ethoxybenzyl)-3-azaglutaric acid-di-tert-butyl ester

溶剂

toluene

N,N-dimethylformamide

反应条件

后处理

1. 1
   workup.STIRRINGit is stirred for another three hours
2. 2
   其他The organic phase is separated
3. 3
   其他dried on magnesium sulfate
4. 4
   过滤filtered
5. 5
   浓缩concentrated by evaporation
6. 6
   其他The oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine
7. 7
   浓缩The product fractions are concentrated by evaporation in a vacuum
8. 8
   其他dried

实验过程

13.2 g (30 mmol) of N-benzyl-2-(4-hydroxybenzyl)-3-azaglutaric acid-di-tert-butyl ester (Example b) is dissolved in 50 ml of anhydrous N,N-dimethylformamide and mixed at 0° C. under argon with 1.31 g (33 mmol) of sodium hydride dispersion (60% in mineral oil). The batch is allowed to stir for 15 minutes, then 8.05 g (51.7 mmol) of ethyl iodide is added, the reaction temperature is allowed to increase to room temperature and it is stirred for another three hours. For working-up, the batch is taken up in toluene and shaken out several times against aqueous sodium bicarbonate solution. The organic phase is separated, dried on magnesium sulfate, filtered and concentrated by evaporation. The oily residue is chromatographed for purification on silica gel with hexane/diethyl ether/triethylamine. The product fractions are concentrated by evaporation in a vacuum and dried.

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