Sodium Hydroxide → tert-butyl 2-(2-(4-methoxy-N,2,6-trimethylphenyl-sulfonamido)ethoxy)acetate

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Reaction Conditions

Reaction Steps

n-Bu4NCl (39 g, 140.1 mmol) was added to a solution of N-(2-hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide (116 g, 424.4 mmol) in toluene (750 ml) and the mixture was cooled to 0° C. Aqueous 35% strength NaOH solution (1,000 ml) was then added. Bromoacetic acid tert-butyl ester (93 ml, 636.6 mmol) was then added dropwise to the reaction mixture and the mixture was stirred at room temperature for 2 hours. The organic phase was separated off, washed with water (3×750 ml), dried over Na2SO4 and concentrated in vacuo. Purification was carried out by chromatography on silica gel (heptane/ethyl acetate 4:1). The yield was 124.6 g (76%).

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