반응 #8524

반응 방정식

2,3,4-trifluoroaniline

methyl D-lactate

2,6-lutidine

hydrochloric acid

trifluoromethanesulfonic acid

→

title compound

수율 90.0%

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

수율 90.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도Under ice-cooling
2. 2
   온도Then it was cooled to 0° C. again
3. 3
   workup.STIRRINGThe mixture was stirred at the same temperature for 17 hours
4. 4
   추출the mixture was extracted with dichloromethane
5. 5
   세척The extract was washed with a saturated aqueous solution of sodium chloride
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   기타After evaporating the solvent
9. 9
   기타the residue thus obtained

실험 절차

Under ice-cooling, methyl D-lactate (8.5 g) and 2,6-lutidine (11.4 g) were dissolved in dichloromethane (100 ml). After dropping anhydrous trifluoromethanesulfonic acid (25.4 g), the mixture was heated to room temperature and stirred for 30 minutes. Then it was cooled to 0° C. again and a solution (30 ml) of 2,3,4-trifluoroaniline (12.0 g) in dichloromethane was dropped therein to. The mixture was stirred at the same temperature for 17 hours. To the resultant solution, hydrochloric acid (0.5 mol/l) was added and the mixture was extracted with dichloromethane. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and filtered. After evaporating the solvent, the residue thus obtained was subjected to silica gel column chromatography. Thus, 17.1 g (90%) of the title compound was obtained as an oily substance. The optical purity determined by HPLC was 97% ee.

출처