Реакция #8545

Уравнение реакции

Methyl2-(2,3,4-trifluoroanilino)propionate

phosphate

hydrochloric acid

→

title compound

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

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter adding α-chymotrypsin (manufactured by Sigma; 0.2 g)
2. 2
   workup.STIRRINGThe mixture was further stirred for 16 hours
3. 3
   Другоеthe liquid reaction mixture
4. 4
   Фильтрацияwas filtered through celite
5. 5
   Другоеseparated
6. 6
   ПромывкаThe organic layer was washed with a 5% aqueous solution of sodium hydrogencarbonate
7. 7
   Сушкаa saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
8. 8
   ДругоеNext, the solvent was evaporated under reduced pressure to thereby give methyl (2S)-2-(2,3,4-trifluoroanilino)propionate (0.43 g)
9. 9
   ДругоеOn the other hand, the all aqueous layers obtained by the separation
10. 10
    Экстракцияfollowed by extraction with IPE
11. 11
    СушкаThe organic layer was dried over anhydrous magnesium sulfate
12. 12
    Другоеevaporated

Методика

Methyl2-(2,3,4-trifluoroanilino)propionate (1.0 g) was suspended in a 0.1 M phosphate buffer solution (pH 6.5; 200 ml). After adding α-chymotrypsin (manufactured by Sigma; 0.2 g), the mixture was gently stirred. The mixture was further stirred for 16 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 (2S)-2-(2,3,4-trifluoroanilino)propionate (0.43 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 (0.47 g). The optical purity of this product was 92% 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 29.

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