Réaction #8544

Équation de réaction

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

phosphate

hydrochloric acid

→

title compound

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

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter adding Protease N (
2. 2
   workup.STIRRINGThe mixture was further stirred for 14 hours
3. 3
   Autrethe liquid reaction mixture
4. 4
   Filtrationwas filtered through celite
5. 5
   Autreseparated
6. 6
   LavageThe organic layer was washed with a 5% aqueous solution of sodium hydrogencarbonate
7. 7
   Séchagea saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
8. 8
   AutreNext, the solvent was evaporated under reduced pressure to thereby give methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (0.94 g)
9. 9
   AutreOn the other hand, the all aqueous layers obtained by the separation
10. 10
    Extractionfollowed by extraction with IPE
11. 11
    SéchageThe organic layer was dried over anhydrous magnesium sulfate
12. 12
    Autreevaporated

Mode opératoire

Methyl 2-(2,3,4-trifluoroanilino)propionate (2.0 g) was suspended in a 0.1 M phosphate buffer solution (pH 6.5; 400 ml). After adding Protease N (manufactured by Amano Seiyaku, originating in a bacterium belonging to the genus Bacillus; 0.4 g), the mixture was gently stirred. The mixture was further stirred for 14 hours while maintaining at 30° C. After adding methylene chloride, the liquid reaction mixture was filtered through celite to eliminate denatured protein and then separated. The organic layer was washed with a 5% aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. Next, the solvent was evaporated under reduced pressure to thereby give methyl (2R)-2-(2,3,4-trifluoroanilino)propionate (0.94 g). The optical purity of this product was 98% ee. On the other hand, the all aqueous layers obtained by the separation were combined and adjusted to pH 2 with 10% hydrochloric acid followed by extraction with IPE. The organic layer was dried over anhydrous magnesium sulfate and evaporated. Thus, the title compound was obtained as a crude product (0.96 g). The optical purity of this product was 96% ee. Further, the crude product was recrystallized from a solvent mixture of isopropyl ether with hexane. Thus, the title compound of 100% ee was obtained. The 1H-NMR and IR spectral data of this product was identical with those of the compound obtained in Example 28.

Source