methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate → 4-(4(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acid

Participants

Reaction Steps

To a stirred solution of methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoate (370 mg, 0.797 mmol) in dioxane (8 ml) was added a solution of LiOH monohydrate (43.5 mg, 1.04 mmol) in water (2 ml) (0.1M solution 4:1 dioxane/water). The reaction was stirred for 5 hours, then diluted with dichloromethane and 2N HCl. The aqueous phase was extracted with dichloromethane and the combined organic layers were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography to give 4-(4-(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acid (0.253 g).

Provenance & Evidence