Triethylamine → (S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoate

Participants

Reaction Steps

Nα -Tert.-butoxycarbonyl-NG -nitro-L-arginine (1.60 g) and L-tyrosine benzyl ester p-toluenesulfonate (2.22 g) are dissolved in anhydrous chloroform (20 ml), and thereto are added triethylamine (1.40 ml) and further 1-methanesulfonyloxy-1,2,3-benzotriazole (1.05 g) and the mixture is stirred at room temperature for 20 hours. After the reaction, to the reaction mixture are added ethyl acetate and water. The ethyl acetate layer is separated, washed with water, a saturated aqueous sodium hydrogen carbonate, water, an aqueous citric acid solution and water in order and then dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off, and the resulting residue is dissolved in chloroform, subjected to chromatography by using silica gel (20 g) and eluted with chloroform to give amorphous powder of N-(Nα -tert.-butoxycarbonyl-NG -nitro-L-arginyl)-L-tyrosine benzyl ester (2.0 g).

Provenance & Evidence