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

HRID 618352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618352
[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]

Komponenten

4

Edukt 1

HCID 74082814-Nitro-L-phenylalanine methyl ester

Produkt 1

HCID 206108304-Amino-L-phenylalanine methyl esterAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f1c79c95b01e46d1a72341d717ab9e1b
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952381

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