Reacción #68041

Ecuación de reacción

ethyl (2E)-3-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acrylate

trifluoroacetic acid

→

ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acrylate

Rendimiento 80.4%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroThe solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and ethyl acetate
3. 3
   workup.ADDITIONwere added
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónthe aqueous layer was extracted with ethyl acetate
6. 6
   Lavadowashed with aqueous saturated sodium chloride solution
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure
9. 9
   OtroThe residue thus obtained
10. 10
    Otrowas purified by silica gel column chromatography [eluent; chloroform:methanol=5:1]

Procedimiento

To 1 mL of a chloroform solution containing 0.10 g of ethyl (2E)-3-(1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acrylate, 1 mL of trifluoroacetic acid was added and stirred for 2 hours. The solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and ethyl acetate were added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=5:1] to give 68 mg of ethyl (2E)-3-(1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acrylate as a yellow oil.

Fuente