Hydrochloric Acid → [Rac]-2-[1-methyl-3-oxo-3-phenyl-(z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid

Participants

Reaction Steps

0.333 g (0.56 mmol) [rac]-2-[1-Methyl-3-oxo-3-phenyl-(Z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid ethyl ester were dissolved in THF/EtOH 1:1 (10 ml) and treated with 1.4 ml (1.4 mmol) aqueous sodium hydroxide solution (1 molar) and the reaction mixture was stirred for 1 hour at room temperature. It was then acidified with 1N hydrochloric acid and extracted with dichloromethane. The combined organic phases were dried over MgSO4 and evaporated. Purification by flash-chromatography (silica gel, eluent: gradient of dichloromethane and methanol) gave 0.218 g (69%) [rac]-2-[1-methyl-3-oxo-3-phenyl-(Z)-propenylamino]-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid as light yellow amorphous solid.

Provenance & Evidence