p-Toluenesulfonic acid → N-(4-ethylphenyl)alanine Methyl Ester

HRID 860320Notes

Reaction equation

HRID 860320 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[C:11]([O:16][CH3:17])(=[O:15])[C:12]([CH3:14])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H]>C(O)C.[Pd]>[CH3:17][O:16][C:11](=[O:15])[C@H:12]([CH3:14])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7468p-AminoacetophenoneHCID 11748Methyl pyruvateHCID 178418361HCID 178418361, compound

Product 1

HCID 54481932N-(4-ethylphenyl)alanine Methyl Ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.68 g (5 mmol) of 4′-aminoacetophenone (Aldrich), 0.60 mL of 90% methyl pyruvate (Aldrich) and 0.05 g (0.25 mmol) of p-toluenesulfonic acid in ethanol was hydrogenated in the presence of a catalytic amount of 10% Pd/C at from 30 to 15 psi of hydrogen for 16 hours. The catalyst was removed by filtering the reaction mixture through Celite and the solvent was evaporated to provide the crude product. The product was purified by column chromatography (silica gel using 1:9 EtOAc/hexanes as the eluant) to provide the title compound.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering the reaction mixture through Celite
  3. customthe solvent was evaporated
  4. customto provide the crude product
  5. customThe product was purified by column chromatography (silica gel using 1:9 EtOAc/hexanes as the eluant)

Sources & evidence

ORD record
ord-9db118a7456343f29a28f61bee34af99
Source dataset
uspto-grants-2006_12
Patent number
US07153847B2

Reaction notes

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