Reaction #8543

Reaction equation

(2R)-2-(2,3,4-trifluoroanilino)propionic acid

ethanol

hydrochloric acid

→

title compound

Ethyl (2R)-2-(2,3,4-trifluoroanilino)propionate

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   OtherThe liquid reaction mixture
3. 3
   Temperaturewas heated
4. 4
   Temperatureunder reflux for 6 hours
5. 5
   Otherthe solvent was evaporated
6. 6
   workup.ADDITIONTo the obtained residue was added chloroform (10 ml)
7. 7
   WashNext, the organic layer was washed with a saturated aqueous solution of sodium chloride and water
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   OtherAfter evaporating the solvent

Procedure

(2R)-2-(2,3,4-trifluoroanilino)propionic acid (219 mg; 99% ee) was dissolved in ethanol (2 ml) and hydrochloric acid (5 mol/l; 0.2 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 (245 mg) as a pale yellow oily substance. The optical purity of the product was 98% ee. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 7.

Source