Sodium Hydroxide → 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylic acid

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Reaction Steps

A mixture of ethyl 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylate (0.570 g, 1.784 mmol) in NaOH (1 N aqueous, 10 mL, 10 mmol) was stirred at ambient temperature for about 72 h. The mixture was partitioned with DCM (10 mL). The aqueous phase was acidified to about pH=4 by addition of 6 N aqueous HCl. The solution was partitioned with DCM (10 mL). The aqueous phase was washed with DCM (2×10 mL). The organic layers were combined, dried over anhydrous MgSO4, and concd under reduced pressure to give 4-((N,N-diethylsulfamoyl)methyl)-2-ethylcyclopentanecarboxylic acid (0.375 g, 72%) as yellow oil: LC/MS (Table 1, Method b) Rt=1.95 min; MS m/z: 292 (M+H)+.

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