Ethyl Acetate → 1-(2-Fluorophenyl)-2-methoxy-2-oxoethanaminium chloride

HRID 525350Notes

Reaction equation

HRID 525350 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])[C:3]([OH:5])=[O:4].S(Cl)([Cl:15])=O.[CH3:17]COC(C)=O>CO.CCCCCC>[Cl-:15].[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:2]([NH3+:1])[C:3]([O:5][CH3:17])=[O:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 5800732-Fluoro-DL-phenylglycine

Product 1

HCID 898139611-(2-Fluorophenyl)-2-methoxy-2-oxoethanaminium chloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a suspension of 2-amino-2-(2-fluorophenyl)acetic acid (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (2 g, 11.8 mmol) in MeOH (40 mL) was added thionyl chloride (1.54 g, 13 mmol) dropwise at −10° C. The resulting reaction mixture was stirred for 12 hours at reflux. After completion of the reaction (monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was cooled to ambient temperature and then concentrated under reduced pressure. The residue was recrystallized with MeOH and diethyl ether to afford 1-(2-fluorophenyl)-2-methoxy-2-oxoethanaminium chloride, 2.5 g (96.30%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 3H), 7.60-7.50 (m, 2H), 7.36-7.29 (m, 2H), 5.45 (s, 1H), 3.73 (s, 3H). m/z (ESI) 184.2 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureat reflux
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized with MeOH and diethyl ether

Sources & evidence

ORD record
ord-ece702b57446445fbc8cc0bdb4074e6d
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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