4-Nitro-L-phenylalanine methyl ester → 4-Amino-L-phenylalanine methyl ester

HRID 618352Notes

Reaction equation

HRID 618352 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[NH2:5]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[NH2:5]

Participants

4

Reactant 1

HCID 74082814-Nitro-L-phenylalanine methyl ester

Product 1

HCID 206108304-Amino-L-phenylalanine methyl esterYield 102.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the product from Step A (5.08 g) in MeOH (75 mL) was added 10% Pd/C (900 mg) in a Parr bottle. This was then shaken on a Parr shaker under 50 psi H2 at room temperature for 4.5 hours. The catalyst was filtered through celite, the solvent removed under vacuum and the crude product purified by reverse phase preparatory HPLC to yield 4.5 g of p-amino-phenylalanine methyl ester, N-isobutyl carbamate, trifluoroacetate as a hygroscopic yellow solid.

Workup

  1. filtrationThe catalyst was filtered through celite
  2. customthe solvent removed under vacuum
  3. customthe crude product purified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-f1c79c95b01e46d1a72341d717ab9e1b
Source dataset
uspto-grants-1999_09
Patent number
US05952381

Reaction notes

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