Reaction #1552041

Reaction equation

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

phenylalanine

2-(phenylseleno)ethanol

THF

→

N-acetylphenylalanine 2-(phenylseleno)ethyl ester

Solvents

ethyl acetate

Conditions

Workup

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

Procedure

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