methyl (2Z)-2-(acetylamino)-3-(4-amino-3-isopropylphenyl)acrylate → methyl N-acetyl-4-amino-3-isopropylphenylalaninate

HRID 488652Notes

Reaction equation

HRID 488652 reaction equation
[C:1]([NH:4]/[C:5](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=1)/[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([NH:4][C@H:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 86585325methyl (2Z)-2-(acetylamino)-3-(4-amino-3-isopropylphenyl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 69803103methyl N-acetyl-4-amino-3-isopropylphenylalaninate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

methyl (2Z)-2-(acetylamino)-3-(4-amino-3-isopropylphenyl)acrylate (752 mg, 2.72 mmole) and 10% Pd/C (143 mg) stirred in ethanol (20 mL) under 1 atmosphere of hydrogen for 16 hours. The mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to provide the titled compound.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-40f018eea4dd47d8859cea3850569147
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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