Triethylamine → N-(3-benzoylphenyl) 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide

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Reaction Steps

To a solution of 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxylic acid (944 mg; 1.2 eq.; 3.05 mmoL), prepared as described above, and 3-aminobenzophenone (500 mg; 2.54 mmol) in methylene chloride (0.15M) was added triethylamine (0.46 mL) at room temperature under nitrogen with stirring, followed by addition of bis(2-oxo-3-oxazolidinyl)phosphinic chloride (773 mg; 1.2 eq) and the resulting mixture was stirred at ambient temperature for 16 hours. This mixture was concentrated to an oil on a rotory evaporator which was partitioned between ethyl acetate (30 mL) and sodium bicarbonate (30 mL). The aqueous phase was extracted twice with ethyl acetate and the resulting combined organic layers were washed with brine and dried magnesium sulfate. After filtering, the solvent was removed to yield the title compound (1.43 g) as a thick orange oil. The compound was further purified by flash chromatography on silica gel to yield 1010 mg (82% yield) N-(3-benzoylphenyl) 2-(3-pyridinyl)-3-tert-butoxycarbonyl-4-thiazolidinecarboxamide as a white foam.

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