Triacetoxyperiodinane → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-formyl-1,3-thiazole-5-carboxylate

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Reaction Steps

Ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate obtained by the method described in Example (27b) (0.17 g, 0.36 mmol) was dissolved in dichloromethane (8 mL). The Dess-Martin reagent (0.2 g, 0.48 mmol) was added, and the mixture was stirred at room temperature for 45 minutes. Saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 1/1, 1/3) to obtain 0.16 g of the title compound as a pale yellow solid (92%).

Provenance & Evidence