Reacción #1375812

Ecuación de reacción

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

Disolventes

toluene

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente