Methanol → Methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochloride

HRID 1844950Notes

Reaction equation

HRID 1844950 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1)[C:3]([OH:5])=[O:4].S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[CH3:19][O:4][C:3](=[O:5])[CH:2]([NH2:1])[CH2:6][C:7]1[CH:8]=[C:9]([F:14])[CH:10]=[C:11]([F:13])[CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27370453,5-Difluorophenylalanine

Product 1

HCID 66940454Methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochlorideYield 100%

Procedure

1.05 g (5.0 mmol) of 2-amino-3-(3,5-difluoro-phenyl)-propionic acid (1.05 g, 5 mmol) was dissolved in 30.0 mL of MeOH, then 1.0 mL of thionyl chloride was added dropwise. The mixture was refluxed overnight. Evaporation of the solvent yielded the solid 2-Amino-3-(3,5-difluoro-phenyl)-propionic acid methyl ester HCl salt (1.26 g, 100%), and it was used directly in the next step.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2f3559b66d7a4cc3b7e6a0c30990da82
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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