Reaktion #427619

Reaktionsgleichung

Trichloroacetyl chloride

dichloromethane

tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate

→

tert-butyl cis-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate

Ausbeute 76.0%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThe solvent was distilled away under reduced pressure
2. 2
   workup.ADDITIONa saturated aqueous ammonium chloride solution and ethyl acetate were added
3. 3
   SonstigeThe organic layer was collected
4. 4
   Waschenwashed with saturated saline
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
7. 7
   SonstigeThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0 to 3:1), diisopropylether
8. 8
   workup.ADDITIONwas added
9. 9
   Filtrationsolid matter was collected by filtration

Vorschrift

Trichloroacetyl chloride (0.55 ml) was added dropwise to a dichloromethane (17 ml) suspension containing tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (1.74 g) and triethylamine (1.38 ml) under ice cooling, followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure, and a saturated aqueous ammonium chloride solution and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0 to 3:1), diisopropylether was added, solid matter was collected by filtration, and a white solid of tert-butyl cis-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (1.26 g) was thus obtained.

Quelle