Ammonium formate → (RS) Methyl 3-{5-[2-(4-amino-3-hydroxy-phenyl)-acetylamino]-pyridin-2-yl}-butanoate

HRID 49720

Reaktionsgleichung

Reaktionsgleichung von HRID 49720
[OH:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([CH3:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([CH:21]([CH3:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[N:19][CH:20]=2)=[O:13])=[CH:3][C:2]=1[OH:1]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 17946659(RS) methyl 3-{5-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-2-yl}-butanoate

Produkt 1

HCID 17946638(RS) Methyl 3-{5-[2-(4-amino-3-hydroxy-phenyl)-acetylamino]-pyridin-2-yl}-butanoateAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of (RS) methyl 3-{5-[2-(3-hydroxy-4-nitrophenyl)-acetylamino]-pyridin-2-yl}-butanoate (2.0 g, Reference Example 25) in ethanol (80 mL), at 60° C., was treated with ammonium formate (4.0 g) and 10% palladium on charcoal (0.5 g). After stirring at 60° C. for 1 hour the reaction mixture was cooled and then filtered. The filtrate was evaporated and the residue was dissolved in ethyl acetate. This solution was washed twice with water, then dried over magnesium sulphate and then evaporated to give the title compound (1.37 g) as an oil.

Aufarbeitung

  1. temperaturewas cooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThis solution was washed twice with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c5851f05f1e04dd48d0249cc66ba9d27
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706738B2

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