Methanol → 3-Amino-3-(3-bromo-5-fluorophenyl)propionic acid methyl ester

HRID 526360Notes

Reaction equation

HRID 526360 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([Br:14])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([Br:14])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 712589843-Amino-3-(3-bromo-5-fluorophenyl)propanoic acid

Product 1

HCID 712589093-Amino-3-(3-bromo-5-fluorophenyl)propionic acid methyl esterYield 93%

Conditions

Temperature
0 °C

Procedure

1.59 g (6.05 mmol) 3-amino-3-(3-bromo-5-fluorophenyl)propionic acid were suspended in 24.5 ml methanol and the mixture cooled to 0° C. 0.66 ml (9.08 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 10 g silica gel (dichloromethane/ethanol 100/0-95/5-90/10) gave 1.55 g (93%) 3-amino-3-(3-bromo-5-fluorophenyl)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-0def4bfc0b194c7fade004927ed841d1
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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