Methanol → 4-Chloro-DL-phenylalanine methyl ester hydrochloride

HRID 590737Notes

Reaction equation

HRID 590737 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[ClH:1].[NH2:8][CH:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][CH:12]=1)[C:9]([O:11][CH3:18])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7361904-Chloro-L-phenylalanine

Product 1

HCID 27332774-Chloro-DL-phenylalanine methyl ester hydrochlorideYield 99%

Procedure

While under nitrogen, a stirred suspension of 4-chlorophenylalanine (2.50 g, 12.5 mmol) in anhydrous methanol (18 mL) was cooled in an ice-water bath and carefully treated with thionyl chloride (1.00 mL, 13.8 mmol). After stirring for 10 min, and the cooling bath was removed and the mixture was allowed to warm to room temperature. A reflux condenser was attached, and the slurry was warmed to 55° C. After stirring overnight, the mixture was cooled to room temperature, concentrated and dried under reduced pressure to give methyl 2-amino-3-(4-chlorophenyl)propanoate hydrochloride (3.13 g, 99%) as a white solid. ESI+ MS found for C10H12ClNO2 m/z 214.0 (M+H).

Workup

  1. temperaturewas cooled in an ice-water bath
  2. customthe cooling bath was removed
  3. customA reflux condenser was attached
  4. temperaturethe slurry was warmed to 55° C
  5. stirringAfter stirring overnight
  6. temperaturethe mixture was cooled to room temperature
  7. concentrationconcentrated
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-9944c14968a54fe796f0126f5e0430cd
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Reaction notes

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