Hydrochloric Acid → Methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

HRID 8444

Reaktionsgleichung

Reaktionsgleichung von HRID 8444
[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].Cl.[CH3:17]O>>[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]([O:8][CH3:17])=[O:7]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67366567(2S)-2-(2,3,4-trifluoroanilino)propionic acid

Produkt 1

HCID 10125210Methyl (2S)-2-(2,3,4-trifluoroanilino)propionate

Versuchsvorschrift

(2S)-2-(2,3,4-trifluoroanilino)propionic acid (1.1 g; 99% ee) was dissolved in methanol (10 ml) and hydrochloric acid (5 mol/l; 1 ml) was added thereto at room temperature. The liquid reaction mixture was heated under reflux for 6 hours and then the solvent was evaporated. To the obtained residue was added chloroform (10 ml). Next, the organic layer was washed with a saturated aqueous solution of sodium chloride and water and dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography (ethyl acetate-normal hexane=1:4) to give the title compound (1.17 g) as an oily substance. The optical purity of the product was 99% ee. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 5.

Aufarbeitung

  1. customat room temperature
  2. customThe liquid reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux for 6 hours
  5. customthe solvent was evaporated
  6. additionTo the obtained residue was added chloroform (10 ml)
  7. washNext, the organic layer was washed with a saturated aqueous solution of sodium chloride and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter evaporating the solvent

Quellen und Nachweise

ORD-Eintrag
ord-986c58db94c34ad9b522d1f578e9a935
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087778B2

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