Reaktion #1919

Reaktionsgleichung

3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid

thionyl chloride

1-amino-6,11-dihydrodibenz[b,e]oxepin-11-one

→

Compound 1

Ausbeute 30.0%

1-(3,3,3-Trifluoro-2-hydroxy-2-methylpropanoylamino)-6,11-dihydrodibenz[b,e]oxepin-11-one

Ausbeute 30.0%

Lösungsmittel

ethyl acetate

dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigeat -15° C.
3. 3
   workup.STIRRINGthe mixture was stirred overnight at room temperature
4. 4
   WaschenThe organic layer was washed successively with a 5% aqueous solution of sodium bicarbonate
5. 5
   Trocknena saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
6. 6
   FiltrationAfter the drying agent was filtered off
7. 7
   Einengenthe organic layer was concentrated under reduced pressure
8. 8
   SonstigeThe obtained oily residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Vorschrift

In dimethylacetamide (3 ml) was dissolved 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid (0.17 g, 1.1 mmol), and thionyl chloride (80 μl, 1.1 mmol) was added thereto at -15° C., followed by stirring at -15 to -5° C. for one hour. To this reaction mixture was added 1-amino-6,11-dihydrodibenz[b,e]oxepin-11-one obtained in Reference Example 4 (0.17 g, 0.77 mmol), and the mixture was stirred overnight at room temperature. After concentration of the reaction mixture under reduced pressure, the obtained oily residue was dissolved in ethyl acetate (20 ml). The organic layer was washed successively with a 5% aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), followed by trituration with hexane to give Compound 1 (80 mg, 30%).

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