Methyl 3-amino-2-methylpropanoate → 3-(4-Methoxy-quinolin-2-ylamino)-2-methyl-propionic acid methyl ester

HRID 2415132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415132
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5](OS(C(F)(F)F)(=O)=O)[CH:4]=1.[CH3:21][O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][NH2:26]>C(#N)C>[CH3:21][O:22][C:23](=[O:28])[CH:24]([CH3:27])[CH2:25][NH:26][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Komponenten

4

Edukt 2

HCID 10486829Methyl 3-amino-2-methylpropanoateHCID 235256351,1,1-Trifluoromethanesulfonic acid 4-methoxyquinolin-2-yl ester

Produkt 1

HCID 698371313-(4-Methoxy-quinolin-2-ylamino)-2-methyl-propionic acid methyl esterAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1,1,1-trifluoromethanesulfonic acid 4-methoxyquinolin-2-yl ester [from Example 1b] (2.03 g, 6.61 mmol) and 3-amino-2-methyl-propionic acid methyl ester (1.5 eq, 1.52 g, 9.91 mmol) in acetonitrile (25 mL) was heated at reflux for five days. It was cooled to room temperature and evaporated to an oil. The crude product was purified via column chromatography on silica (1:1 ethyl acetate/hexane) to give the product (0.75 g, 42%) as an orange oil. [M+H]+ 275.

Aufarbeitung

  1. temperatureat reflux for five days
  2. customevaporated to an oil
  3. customThe crude product was purified via column chromatography on silica (1:1 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-58ec150cafc145d59574ae66d93d4135
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06818655B2

Notizen zur Reaktion

Wird geladen…