Diisopropylethylamine → (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-N'-(4-iodopyridin-2-yl)benzohydrazide

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반응 단계

(S)-4-(5,5-Dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acid (1500 mg, 4.82 mmol) was dissolved in DMF (9.636 mL) at room temperature. To the reaction mixture were added N-ethyl-N-isopropylpropan-2-amine (2.514 mL, 14.45 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (1.832 g, 4.82 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) and 2-hydrazinyl-4-iodopyridine (1.132 g, 4.82 mmol). The vial was sealed and immersed in a 55° C. oil bath. After stirring overnight, LC-MS indicated complete conversion. After cooling to room temperature, the reaction mixture was transferred to water in a flask in an ice/water bath. The solution was washed with DCM (3×50 mL). The combined organic layers were then washed with water (2×50 mL) and brine (50 mL). The organic extract was dried over Na2SO4. The residual material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 10% MeOH in DCM, to provide (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-N′-(4-iodopyridin-2-yl)benzohydrazide (1.53 g, 2.90 mmol, 60.1% yield) as an off-white solid. m/z (ESI) 529.0 (M+H)+.

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