Hydrochloric Acid → (2S)-2-(2,3,4-trifluoroanilino)propionic acid

HRID 458175

Reaction equation

HRID 458175 reaction equation
[F:1][C:2]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:3]=1[NH:4][C@@H:5]([CH3:9])[C:6]([OH:8])=[O:7].C1([C@@H](N)C)C=CC=CC=1.Cl>>[F:1][C:2]1[C:13]([F:14])=[C:12]([F:15])[CH:11]=[CH:10][C:3]=1[NH:4][C@@H:5]([CH3:9])[C:6]([OH:8])=[O:7]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67369703HCID 67369703, compound

Product 1

HCID 67366567(2S)-2-(2,3,4-trifluoroanilino)propionic acidYield 96%

Procedure

To (2S)-2-(2,3,4-trifluoroanilino)propionic acid•(S)-1-phenylethylamine salt (1.0 g; 99% ee) were added IPE (20 ml) and hydrochloric acid (1 mol/l) until the pH value reached 1 and the resultant mixture was stirred at room temperature for 1 hour. The organic layer was dried over anhydrous magnesium sulfate. After evaporating the solvent, 618 mg of the title compound was obtained as colorless crystals. The optical purity of this product was 99% ee. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 23.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-13c76af55b6d416fb24bc04ff8a3e530
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Linked notes

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