반응 #72163

반응 방정식

lithium hydroxide

ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate

Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate

Water

→

title compound

수율 80.8%

2-(3-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylic acid

수율 80.8%

용매

methanol THF

반응 조건

후처리

1. 1
   세척the mixture was washed with ethyl acetate
2. 2
   workup.ADDITIONA 1 N aqueous hydrochloric acid solution (1 mL) was added to the aqueous layer
3. 3
   추출followed by extraction with ethyl acetate
4. 4
   건조The combined organic layers were dried over anhydrous magnesium sulfate
5. 5
   여과filtered
6. 6
   농축the filtrate was concentrated under reduced pressure
7. 7
   세척washed in diethyl ether

실험 절차

A 2 N aqueous lithium hydroxide solution (0.72 mL, 1.43 mmol) was added to a mixed solution of ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate obtained in Example (221c) (61 mg, 0.14 mmol) in methanol/THF (1.5 mL/1 mL) at room temperature, and the mixture was stirred at 40° C. for 70 minutes. Water was added to the reaction solution, and then the mixture was washed with ethyl acetate. A 1 N aqueous hydrochloric acid solution (1 mL) was added to the aqueous layer, followed by extraction with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting solid was suspended and washed in diethyl ether to obtain 45 mg of the title compound as a white solid (79%).

출처