Acetic Anhydride → HCID 20094381, compound

Participants

Reaction Steps

To a solution of 5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]-1-(2-hydroxyethyl)indoline-7-carboxamide (60 mg) in methylene chloride (3 ml) were added triethylamine (24 μl) and acetic anhydride (13 μl) with stirring under ice cooling, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and to the concentrate was added water. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution and water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in methylene chloride (2 ml). To the solution was added trifluoroacetic acid (0.5 ml), the mixture was stirred at room temperature for 30 minutes, and the reaction mixture was concentrated under reduced pressure. To the concentrate was added a saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of chloroform and methanol (7/1) as eluent to give 41 mg of 1-(2-acetoxyethyl)-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide as an oil.

Provenance & Evidence