Réaction #1552041

Équation de réaction

1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride

phenylalanine

2-(phenylseleno)ethanol

THF

→

N-acetylphenylalanine 2-(phenylseleno)ethyl ester

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Extractionextracted with 50 ml of a 0.5 M HCl solution
2. 2
   SéchageThe organic phase was dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Autrethe solvent was removed in vacuo
5. 5
   AutrePurification by column chromatography (PE:EE=2:1)
6. 6
   Autreyielded 2.9 g (91% of th., 98% of lit.) of a yellowish liquid

Mode opératoire

In a 50 ml round bottomed flask, 2.55 g (13.3 mmol) of 1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride and 1.7 g of (8.2 mmol) phenylalanine were added to a solution of 1.87 g (9.3 mmol) of 2-(phenylseleno)ethanol in 20 ml of THF. The reaction mixture was then stirred for 12 hours at room temperature. The mixture was then diluted with 50 ml of ethyl acetate and extracted with 50 ml of a 0.5 M HCl solution. The organic phase was dried over sodium sulfate, filtered, and the solvent was removed in vacuo. Purification by column chromatography (PE:EE=2:1) yielded 2.9 g (91% of th., 98% of lit.) of a yellowish liquid.

Source