Phenethylamine → HCID 21308260, compound

HRID 1872903Notes

Reaction equation

HRID 1872903 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)C.[N+](C1C=CC([O:25][C:26](=O)[C@H:27]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[NH:28]C(OCC2C=CC=CC=2)=O)=CC=1)([O-])=O.[H][H].CO.C(Cl)(Cl)[Cl:52]>[Pd]>[ClH:52].[C:1]1([CH2:7][CH2:8][NH:9][C:26](=[O:25])[C@H:27]([CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[NH2:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Procedure

2-Phenylethylamine (577 mg, 4.8 mmol) was added to an ethyl acetate solution (50 ml) of N-benzyloxycarbonyl-L-phenylalanine 4-nitrophenyl ester (2.0 g, 4.8 mmol). The mixture was stirred at room temperature for 9 hours. After completion of the reaction, the reaction mixture was washed with a dilute aqueous solution of sodium hydroxide until washings became free from coloring, and then washed with water and saturated brine, and was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.9 g of a condensate. The thus-obtained condensate (1.65 g, 4.3 mmol) was dissolved in a mixed solvent (100:1) of methanol-chloroform, and 10% palladium on carbon (1.65 g) was added to the solution. The mixture was stirred at room temperature for 1 hour in a hydrogen atmosphere. After completion of the reaction, the catalyst was separated by filtration, and the filtrate was concentrated under reduced pressure to obtain 1.13 g of the title compound.

Workup

  1. customAfter completion of the reaction
  2. washthe reaction mixture was washed with a dilute aqueous solution of sodium hydroxide until washings
  3. washwashed with water and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto obtain 1.9 g of a condensate
  7. additionwas added to the solution
  8. customAfter completion of the reaction
  9. customthe catalyst was separated by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ca6f97eba761430d837239d7bf01fca0
Source dataset
uspto-grants-2000_08
Patent number
US06110967

Reaction notes

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