Hydrochloric Acid → Efatutazone

Participants

Reaction Steps

A mixture of t-butyl N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-[4-(2,4dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl]-N-methylcarbamate (1.88 g) and 4N hydrogen chloride in 1,4-dioxane (20 ml) was stirred at room temperature for 23 hours. The reaction mixture was concentrated and water added to the residue. The mixture was neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=2:1 as the eluant to afford the desired compound (0.26 g, mp 209-211° C.).

Provenance & Evidence