p-Toluenesulfonic acid → N-[1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethyl-3-phenylpropyl]-4-chlorobenzamide

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Reaction Steps

A suspension of p-chlorobenzamide (3.02 g, 20.0 mmol), the product from Example 18A (3.24 g, 20.0 mmol), and benzotriazole (2.38 g, 20.0 mmol) in benzene (75 mL) was treated with p-toluenesulfonic acid (190 mg, 1.00 mmol). The solution was heated at reflux under Dean-Stark conditions for 10 hours, then cooled gradually to ambient temperature. The solvent was removed under vacuum and the residue was purified by flash chromatography (elution with 15% EtOAc/hexanes) to provide the title compound (3.63 g) as a white solid.

Provenance & Evidence