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

HRID 1069156Notes

Reaction equation

HRID 1069156 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-022c6d61753e4bd88f03464e42a5aa91
Source dataset
uspto-grants-2001_06
Patent number
US06251944B1

Reaction notes

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