Reacción #748636

Ecuación de reacción

3-Hydroxy-2,2-dimethyl-propionic acid tert-butyl ester

sodium hydride

compound

(2R,4S)-2-Ethyl-4-(5-morpholin-4-yl-pyridin-2-ylamino)-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-nitrophenyl ester

sodium hydrogen carbonate

→

titled compound

Rendimiento 71.3%

(2R,4S)-2-Ethyl-4-(5-morpholin-4-yl-pyridin-2-ylamino)-6-trifluoromethyl-3,4-dihydro-2H-quinolin-1-carboxylic acid 2-tert-butoxycarbonyl-2-methyl-propyl ester

Rendimiento 71.3%

Disolventes

ethyl acetate

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Otrothe organic layer was separated
3. 3
   Lavadowashed with a saturated brine
4. 4
   Secadodried over magnesium sulfate
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=7:3→2:3)

Procedimiento

3-Hydroxy-2,2-dimethyl-propionic acid tert-butyl ester (137 mg) and sodium hydride (60%; 32 mg) were added to a solution of the compound obtained in Example 9 (1) (300 mg) dissolved in tetrahydrofuran (5 ml) and stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, a saturated sodium hydrogen carbonate aq. solution and ethyl acetate were added and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=7:3→2:3) to give the titled compound (227 mg). MS (m/z):607 [M+H]+.

Fuente