Hydrochloric Acid → 3-((2,4,6-Trichloro-N-methylphenylsulfonamido)methoxy)propionic Acid

Participants

Reaction Steps

2,4,6-Trichloro-N-(3-hydroxypropoxymethyl)-N-methylbenzenesulfonamide (363 mg, 1 mmol), 2,2,6,6-tetramethylpiperidin-1-yloxy radical (38 mg, 0.245 mmol) and [bis(acetoxy)iodo]benzene (705 mg, 2.19 mmol) were dissolved in acetonitrile/water (1:1; 8 ml) and the solution was stirred at RT for 30 min. The reaction soln. was then cooled with ice, and 2 N hydrochloric acid (4 ml) and EtOAc (40 ml) were added. The phases were separated and the organic phase was washed with water (3×20 ml) and saturated sodium chloride solution (2×20 ml), dried with Na2SO4 and concentrated i. vac. The compound was taken up in 1 N sodium carbonate soln. (30 ml) and the mixture was extracted with EtOAc (3×20 ml). The aqueous phase was then adjusted to pH 3 with 2 N hydrochloric acid and extracted with EtOAc (3×20 ml). The combined organic phases were washed with water (3×20 ml) and saturated sodium chloride solution (2×20 ml), dried with Na2SO4 and concentrated i. vac. Yield: 310 mg (82%)

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