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

HRID 985664Notes

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

Reactant 2

HCID 313Hydrochloric Acid

HCID 67369703(2S)-2-(2,3,4-trifluoroanilino)propionic acid.(S)-1-phenylethylamine

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

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

Sources & evidence

ORD record: ord-01d1d63a57c94c72a2ed07e98d229794
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872823B1

Reaction notes

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