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

HRID 526342ノート

反応式

HRID 526342 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-75b1b11430954a0db9468824230629ef
出典データセット
uspto-grants-2016_05
特許番号
US09345793B2

反応ノート

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