Diethyl Ether → 1-[4-(4-Fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester

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To a solution of 1-aminocyclopentanecarboxylic acid benzyl ester p-toluenesulfonic acid salt (200 grams, 0.51 mole) and triethylamine (177 mL, 1.27 mole) in water (1 L) and 1,2-dimethoxyethane (1 L) was added 4-(4-fluorophenoxy)benzenesulfonyl-chloride (161 grams, 0.56 moles). The mixture was stirred at room temperature for 16 hours and then most of the solvent was removed by evaporation under vacuum. The mixture was diluted with ethyl acetate and was washed successively with dilute hydrochloric acid solution, water, and brine. The solution was dried over magnesium sulfate and concentrated to leave a brown solid. Trituration with diethyl ether to afforded 1-[4-(4-fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester as a tan solid, 167 grams (70%).

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