Reaktion #49032

Reaktionsgleichung

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

Water

sodium bicarbonate

dichloroacetic acid

→

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

Ausbeute 71.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Extraktionwas then extracted with methylene chloride (2×10 ml)
3. 3
   WaschenThe combined organic layers were washed with aqueous sodium bicarbonate (5-fold dilution of saturated solution, 8 ml) and saturated brine (8 ml)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe resultant residue was purified by silica gel column chromatography (methylene chloride/methanol (40:3))

Vorschrift

The oxime, (E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-isobutyrylamino-ethoxyimino)-methyl]-benzamide (28.8 mg, 47.3 μmol) obtained in Step A was suspended in methylene chloride (1 ml), and dichloroacetic acid (60 ml) and borane-pyridine complex (70 μl) were added thereto at room temperature. The mixture was stirred at room temperature for 2 hours. Water (6 ml) and aqueous sodium bicarbonate (2 ml) were added to the reaction mixture, which was then extracted with methylene chloride (2×10 ml). The combined organic layers were washed with aqueous sodium bicarbonate (5-fold dilution of saturated solution, 8 ml) and saturated brine (8 ml), dried over sodium sulfate, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (methylene chloride/methanol (40:3)) to give 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-isobutyrylamino-ethoxyamino)-methyl]-benzamide (Compound C-35, 20.5 mg, 71%) as a colorless syrup.

Quelle