Methanol → Methyl β-amino-3-chlorobenzenepropanoate

HRID 1394382Notes

Reaction equation

HRID 1394382 reaction equation
S(Cl)(Cl)=O.[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:7][C:8]([OH:10])=[O:9].[CH3:18]O>>[NH2:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:7][C:8]([O:10][CH3:18])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27641783-amino-3-(3-chlorophenyl)propanoic acid

Product 1

HCID 43147869Methyl β-amino-3-chlorobenzenepropanoate

Procedure

Methanol (110 ml) is cooled to −10° C. and slowly admixed with thionyl chloride (12.0 g, 101.2 mmol). 3-Amino-3-(3-chlorophenyl)propionic acid (10.1 g, 50.6 mmol) is added and the mixture is stirred at room temperature overnight. The solution is concentrated to a high extent, under reduced pressure, and partitioned between ethyl acetate (100 ml) and saturated sodium hydrogen carbonate solution (200 ml). The pH of the aqueous phase is above 7. The aqueous phase is again extracted twice with ethyl acetate (100 ml). The combined ethyl acetate phases are dried over sodium sulfate, filtered and concentrated.

Workup

  1. concentrationThe solution is concentrated to a high extent, under reduced pressure
  2. custompartitioned between ethyl acetate (100 ml) and saturated sodium hydrogen carbonate solution (200 ml)
  3. extractionThe aqueous phase is again extracted twice with ethyl acetate (100 ml)
  4. dry with materialThe combined ethyl acetate phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-13eeec91c81b4b058802cc0495e72936
Source dataset
uspto-grants-2008_03
Patent number
US07348357B2

Reaction notes

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