Reacción #1504309

Ecuación de reacción

EDAC

t-butyloxycarbonylglycine

dicyclohexylamine

glycylglycine benzyl ester hydrochloride

→

t-butyloxycarbonylglycylglycylglycine benzyl ester

Rendimiento 86.0%

Disolventes

chloroform

chloroform methylene chloride ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added at -5° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 24 hours
3. 3
   LavadoThe resulting chloroform solution was successively washed twice with a 10% by weight aqueous citric acid solution
4. 4
   SecadoThereafter, the organic phase was dried over anhydrous sodium sulfate
5. 5
   OtroThe solvent was then completely removed in vacuo
6. 6
   Otroto obtain a white oily material
7. 7
   OtroThis was crystallized from hexane

Procedimiento

In 380 ml of a chloroform/methylene chloride/ethyl acetate (7:5:1 by volume) mixed solvent were dissolved 7.13 g (20 mmol) of t-butyloxycarbonylglycine.dicyclohexylamine and 5.18 g (20 mmol) of glycylglycine benzyl ester hydrochloride obtained in Example 1. To this solution, 50 ml of a chloroform solution containing 4.22 g (20 mmol) of EDAC were added at -5° C. with stirring. The resulting mixture was stirred for 24 hours. The resulting chloroform solution was successively washed twice with a 10% by weight aqueous citric acid solution, then twice with water, then twice with a 4% by weight aqueous sodium hydrogen carbonate solution and finally twice with water. Thereafter, the organic phase was dried over anhydrous sodium sulfate. The solvent was then completely removed in vacuo to obtain a white oily material. This was crystallized from hexane to obtain 6.52 g (yield: 86%) of t-butyloxycarbonylglycylglycylglycine benzyl ester as a white solid. This benzyl ester was dispersed, to which 130 ml of 4N HCl/ethyl acetate were added. The mixture was stirred for 4 hours and then the solvent was removed in vacuo to obtain white precipitates. The precipitates were washed well with diethyl ether to obtain 4.63 g (yield: 85%) of glycylglycylglycine benzyl ester hydrochloride as a white solid having the following physical properties:

Fuente