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

HRID 526342Notes

Reaction equation

HRID 526342 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-75b1b11430954a0db9468824230629ef
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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