Реакция #1552041

ord-6f795c9c7dd7420494421229fb03b2f9

Уравнение реакции

CCN=C=NCCCN(C)C.Cl
1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride
N[C@@H](Cc1ccccc1)C(=O)O
phenylalanine
OCC[Se]c1ccccc1
2-(phenylseleno)ethanol
C1CCOC1
THF
CC(=O)N[C@@H](Cc1ccccc1)C(=O)OCC[Se]c1ccccc1
N-acetylphenylalanine 2-(phenylseleno)ethyl ester

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Экстракцияextracted with 50 ml of a 0.5 M HCl solution
  2. 2
    СушкаThe organic phase was dried over sodium sulfate
  3. 3
    Фильтрацияfiltered
  4. 4
    Другоеthe solvent was removed in vacuo
  5. 5
    ДругоеPurification by column chromatography (PE:EE=2:1)
  6. 6
    Другоеyielded 2.9 g (91% of th., 98% of lit.) of a yellowish liquid

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08999323B2uspto-grants-2015_04