Sodium Bicarbonate → HCID 86749070, compound

Participants

Reaction Steps

To a stirred solution of cis-N-benzyl-4-[1-(4-methoxybenzylthio)-1-methylethyl]-2-(4-methoxybenzylthiomethyl )-4-butanelactam (compound No.14-1, 500 mg) in trifluoroacetic acid (4 ml), thioanisol (0.66 ml) and trifluoromethanesulfonic acid (0.50 ml) were added. After stirring for 2 hours at room temperature, the mixture was poured into a mixture of ice and saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and then saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was dissolved in ethanol (3 ml). To the solution sodium borohydride (20 mg) was added and the mixture was stirred for 30 minutes at room temperature. 1N hydrochloric acid was added to the mixture and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 50 mg (18%) of the titled compound.

Provenance & Evidence