HCID 10408174, compound → 6-(4-((4-Chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid methyl ester

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Reaction Steps

To a solution of 6-(4-((4-chlorobenzyl)-methylamino)-phenylsulfanyl)-hexanoic acid methyl ester (840 mg, 2.1 mmol) in methanol (60 mL) and tetrahydrofuran (30 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (504 mg, 2.3 mmol) in distilled water (20 mL). The mixture was heated at reflux for 1 hour. The solution was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (75 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (50 mL), distilled water (50 mL), and brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (50:50:1 ethyl acetate:40-60° C. ether:triethylamine). The title compound was obtained as a colourless oil (759 mg, 87%).

Provenance & Evidence