Réaction #8541

Équation de réaction

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

methanol

hydrochloric acid

→

title compound

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

Conditions de réaction

Traitement

1. 1
   Autreat room temperature
2. 2
   AutreThe liquid reaction mixture
3. 3
   Températurewas heated
4. 4
   Températureunder reflux for 6 hours
5. 5
   Autrethe solvent was evaporated
6. 6
   workup.ADDITIONTo the obtained residue was added chloroform (10 ml)
7. 7
   LavageNext, the organic layer was washed with a saturated aqueous solution of sodium chloride and water
8. 8
   Séchagedried over anhydrous magnesium sulfate
9. 9
   AutreAfter evaporating the solvent

Mode opératoire

(2R)-2-(2,3,4-trifluoroanilino)propionic acid (1.1 g; 98% 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.

Source