Reaktion #49037

Reaktionsgleichung

(E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-methylcarbamoyl-ethoxyimino)-methyl]-benzamide

dichloroacetic acid

→

title compound

Ausbeute 96.7%

3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(3-oxo-isoxazolidin-2-yl methyl)-benzamide

Ausbeute 96.7%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a suspension
2. 2
   workup.STIRRINGAfter the mixture was stirred at room temperature for 13 hours
3. 3
   Sonstigedichloromethane was removed under reduced pressure with a rotary evaporator
4. 4
   workup.ADDITIONthe resultant residue was diluted with 1,2-dichloroethane (300 ml)
5. 5
   workup.STIRRINGThis mixture was stirred at 60° C. for 6 hours
6. 6
   workup.ADDITIONdiluted with ethyl acetate
7. 7
   Waschenwashed sequentially with 0.1 M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
8. 8
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To (E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-methylcarbamoyl-ethoxyimino)-methyl]-benzamide (9.60 g, 15.54 mmol) were added sequentially dichloromethane (300 ml) and borane-pyridine complex (11.70 ml, 115.80 mmol) to give a suspension. This mixture was stirred at room temperature, and dichloroacetic acid (9.51 ml, 115.80 mmol) was added dropwise thereto over 10 minutes. After the mixture was stirred at room temperature for 13 hours, dichloromethane was removed under reduced pressure with a rotary evaporator, and the resultant residue was diluted with 1,2-dichloroethane (300 ml). This mixture was stirred at 60° C. for 6 hours, diluted with ethyl acetate, and washed sequentially with 0.1 M aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (8.28 g, 90% yield).

Quelle