4-Chlorobenzenesulfonyl chloride → Trans-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid

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Reaction Steps

Trans-2-Aminocyclohexanecarboxylic acid (0.150 g, 1.05 mmol) is dissolved in 1.5 ml of water and NaOH (0.09 g, 2.25 mmol) in 1.5 ml of water is added at 0° C. 4-Chlorobenzene sulfonyl chloride (0.243 g, 1.15 mmol) in 1.5 ml of toluene is added. The reaction mixture is stirred at room temperature for 16 hours. The toluene layer is separated and the aqueous layer is washed twice with toluene. The toluene layers are discarded. Ethyl acetate is added to the aqueous layer (15 ml) and 2M HCl until pH<7. The two phases are separated and the aqueous layer is extracted with ethyl acetate (3×15 mL). The combined organic phases are washed with brine (20 ml), dried over MgSO4 and the ethyl acetate is removed under reduced pressure leaving a white solid that is dissolved in toluene (2×10 ml) and concentrated .The product is dried in vacuum.

Provenance & Evidence