Sodium Sulfite → Ethyl 3-{[(4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfonyl)pentyl]amino}phenyl)carbonyl](methyl)amino}-propanoate

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Reaction Steps

To a solution (10 mL) of ethyl 3-{[(4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentyl]amino}phenyl)carbonyl](methyl)amino}-propanoate (263 mg) synthesized in Example A121(1) in acetone was added m-chloroperbenzoic acid (water-containing, purity 69-75%) (344 mg) at 0° C., and the mixture was stirred overnight at room temperature. Saturated aqueous sodium sulfite solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane), then by NH silica gel column chromatography (ethyl acetate) to give the title object compound (104 mg, 37%) as a pale-yellow oil.

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