Reaction #1375811

Reaction equation

N-benzyl-tyrosine-tert-butyl ester

bromoacetic acid-tert-butyl ester

water

potassium carbonate

→

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

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Filtrationit is filtered
3. 3
   Concentrationconcentrated by evaporation in a vacuum
4. 4
   Otherthe residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine
5. 5
   ConcentrationThe product fractions are concentrated by evaporation in a vacuum
6. 6
   Otherdried

Procedure

15.1 g (46.1 mmol) of N-benzyl-tyrosine-tert-butyl ester (Example a) is dissolved in 50 ml of tetrahydrofuran and mixed with 5 ml of water and 9.54 9 (69 mmol) of potassium carbonate. After instillation of 9.89 g (51 mmol) of bromoacetic acid-tert-butyl ester, it is stirred for two days at 65° C. After cooling, it is filtered, concentrated by evaporation in a vacuum and the residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine. The product fractions are concentrated by evaporation in a vacuum and dried.

Source