Methanol → Methyl 3-amino-3-(5-bromopyridin-3-yl)propanoate

HRID 526342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526342
[NH2:1][CH:2]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Br:13])[CH:12]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Br:13])[CH:12]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 212566853-Amino-3-(5-bromopyridin-3-yl)propionic acid

Produkt 1

HCID 57045437Methyl 3-amino-3-(5-bromopyridin-3-yl)propanoateAusbeute 52 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

9.54 g (38.93 mmol) 3-amino-3-(5-bromopyridin-3-yl)propionic acid were suspended in 158 ml methanol and the mixture cooled to 0° C. 4.26 ml (58.39 mmol) thionyl chloride were slowly added. The mixture was stirred at room temperature for 20 hours and concentrated. The residue was treated with saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic part was dried with sodium sulfate and concentrated. Chromatography over silica gel (dichloromethane/ethanol 100/0-50/50) gave 5.84 g (52%) 3-amino-3-(5-bromopyridin-3-yl)-propionic acid methyl ester.

Aufarbeitung

  1. concentrationconcentrated
  2. additionThe residue was treated with saturated sodium hydrogen carbonate solution
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic part was dried with sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-75b1b11430954a0db9468824230629ef
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345793B2

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