Hydrochloric Acid → HCID 15887032, compound

Participants

Reaction Steps

tert-Butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-1H-indol-5-yl]-1-methylethyl]-N-[2-(2-ethoxyphenoxy)ethyl]carbamate (4.45 g) was dissolved in isopropanol (50 ml), and concentrated hydrochloric acid (25 ml) was added portionwise to the solution under ice-cooling with stirring. After the mixture was stirred for 3 hours at room temperature, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture under ice-cooling and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by column chromatography on aminopropyl silica gel (eluent: methylene chloride/methanol=20/1) to give white amorphous (R)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]-propyl]-1-(3-hydroxypropyl)-1H-indole-7-carboxamide (1.27 g). Unpurified mixture was further purified by column chromatography on aminopropyl silica gel (eluent:ethyl acetate/ethanol=7/1) and the purified product was combined with the previously purified product to give white amorphous (R)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-1-(3-hydroxypropyl)-1H-indole-7-carboxamide (2.39 g).

Provenance & Evidence