Sodium Bicarbonate → HCID 68278815, compound

Participants

Reaction Steps

A solution of ethyl 2-[N-(2-ethylbenzenesulphonyl)-N-(2-trimethylsilylethoxymethyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (Intermediate 37, 0.107 g) in concentrated hydrochloric acid (1 ml) and methanol (3 ml) was heated at 80° C. for 1 hour. After cooling to room temperature, the mixture was added drop-wise to a mixture of ice and saturated aqueous sodium hydrogen carbonate solution (25 ml) and then extracted with ethyl acetate (3×15 ml). The combined organic layers were washed with brine (5 ml), dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (0-20%) to give ethyl 2-(2-ethylbenzenesulphonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.041 g) as a white solid.

Provenance & Evidence