L-Alanine → (S)-2-{[1-bromo-4-hydroxy-isoquinoline-3-carbonyl]-amino}-propionic acid

HRID 250344

Reaktionsgleichung

Reaktionsgleichung von HRID 250344
C(O[C:6]([C:8]1[N:9]=[C:10]([Br:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:20][C@H:21]([C:23]([OH:25])=[O:24])[CH3:22].C[O-].[Na+]>CO>[Br:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:20][C@@H:21]([CH3:22])[C:23]([OH:25])=[O:24])=[O:7])[N:9]=1

Komponenten

5

Edukt 3

HCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Produkt 1

HCID 86595466(S)-2-{[1-bromo-4-hydroxy-isoquinoline-3-carbonyl]-amino}-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

400 mg of 1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester and 890 mg of (L)-Alanine was suspended in a 20 ml solution of 0.5 M of sodium methoxide in methanol. The mixture was heated to 160° C. for 12 min using a CEM Discover microwave reactor. The resultant solution was concentrated to ca. 10 ml, and 0.5 N HCl was added until a pH 3 was reached. The solution was extracted three times with ethyl acetate, and the organic fractions dried over sodium sulfate and concentrated to a tan solid; MS (−): m/z 337.14 (M−1)

Aufarbeitung

  1. concentrationThe resultant solution was concentrated to ca. 10 ml, and 0.5 N HCl
  2. additionwas added until a pH 3
  3. extractionThe solution was extracted three times with ethyl acetate
  4. dry with materialthe organic fractions dried over sodium sulfate
  5. concentrationconcentrated to a tan solid

Quellen und Nachweise

ORD-Eintrag
ord-69df67e224fe4843a9a8ed0604bb485d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863292B2

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