Reacción #49004

Ecuación de reacción

water

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

trifluoroacetic acid

sodium cyanoborohydride

→

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe progression of the reaction by TLC
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe organic layer was washed with saturated aqueous sodium bicarbonate
4. 4
   Secadodried over magnesium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH (15:1))
7. 7
   Otrothe resultant crude compound was crystallized from methylene chloride

Procedimiento

To a solution of (E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-ethoxyimino)-methyl]-benzamide (3.62 g, 6.70 mmol) obtained in Step B in methanol (100 ml) were added portionwise trifluoroacetic acid (6.5 ml) and sodium cyanoborohydride (3.78 g, 60.2 mmol) over 2 days while monitoring the progression of the reaction by TLC. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH (15:1)), and the resultant crude compound was crystallized from methylene chloride to give 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-ethoxyamino)-methyl]-benzamide (1.66 g, 46%, as a total of first and second crystals).

Fuente