Hydrogen Peroxide → N-acetylphenylalanine vinyl ester

HRID 1464860Notes

Reaction equation

HRID 1464860 reaction equation
C1([Se][CH2:8][CH2:9][O:10][C:11](=[O:24])[C@H:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:13][C:14](=[O:16])[CH3:15])C=CC=CC=1.OO>C1COCC1.C(Cl)(Cl)Cl>[CH:9]([O:10][C:11](=[O:24])[C@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:13][C:14](=[O:16])[CH3:15])=[CH2:8]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 11069180HCID 11069180, compound

Product 1

HCID 11009857N-acetylphenylalanine vinyl ester

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2.6 g (6.66 mmol) of N-acetylphenylalanine 2-(phenylseleno)ethyl ester in 20 ml of THF, 8 ml of a 30% H2O2 solution were added dropwise within 10 minutes at 0° C., and the solution was stirred at 0° C. for another 30 minutes. After stirring the mixture for 12 hours at room temperature, it was diluted with 80 ml of CHCl3 and extracted with 3×50 ml of water. The organic phases were then dried over sodium sulfate, and the solvent was removed. The residue was taken up in 70 ml of chloroform and was refluxed for 24 hours. After cooling, the solvent was removed. Flash column—chromatography (PE:EE=3:1) yielded 1.3 g (84% of th., 93% of lit.) of a light-yellow liquid.

Workup

  1. stirringAfter stirring the mixture for 12 hours at room temperature
  2. extractionextracted with 3×50 ml of water
  3. dry with materialThe organic phases were then dried over sodium sulfate
  4. customthe solvent was removed
  5. temperaturewas refluxed for 24 hours
  6. temperatureAfter cooling
  7. customthe solvent was removed
  8. customFlash column—chromatography (PE:EE=3:1) yielded 1.3 g (84% of th., 93% of lit.) of a light-yellow liquid

Sources & evidence

ORD record
ord-851fa221374449539c464633e72a3034
Source dataset
uspto-grants-2015_04
Patent number
US08999323B2

Reaction notes

Loading…