반응 #1375812

반응 방정식

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

용매

toluene

N,N-dimethylformamide

반응 조건

후처리

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

실험 절차

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.

출처