Reaktion #76439

Reaktionsgleichung

N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide

3,3,3-trifluoropropionic acid

1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamide

Ausbeute 73.5%

Lösungsmittel

N,N-dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with water
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   ExtraktionThe organic extract
4. 4
   Waschenwas washed with water
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe filtrate was evaporated in vacuo
8. 8
   SonstigeThe residue was purified by flash column chromatography on silica gel
9. 9
   Wascheneluting with ethyl acetate:hexane 1:1

Vorschrift

A mixture of N-(4-chloro-3-methylisothiazol-5-yl)-2-(3-amino-4-hydroxyphenyl)propionamide (0.65 g, 0.002 mol), 3,3,3-trifluoropropionic acid (0.267 g, 0.002 mol) and 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.40 g, 0.002 mol) was stirred in N,N-dimethylacetamide (8 ml) at room temperature for 7 hours and was then allowed to stand at room temperature overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate:hexane 1:1, to give N-(4-chloro-3-methylisothiazol-5-yl)-2-[4-hydroxy-3-(3,3,3-trifluoropropionamido)phenyl]propionamide (0.62 g) as a white solid.

Quelle