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Example ( 27b )

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

Dess-Martin reagent

sodium bicarbonate

→

title compound

수율 94.6%

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

수율 94.6%

용매

dichloromethane

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후처리

1. 1
   추출followed by extraction with dichloromethane
2. 2
   세척The organic layer was washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium bicarbonate solution and brine
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   농축concentration under reduced pressure
5. 5
   기타the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1, 1/1, 1/3)

실험 절차

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%).

출처