Reaction #1375812

Reaction equation

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

Solvents

toluene

N,N-dimethylformamide

Conditions

Workup

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

Procedure

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.

Source