반응 #41649

반응 방정식

ammonium chloride

methyl lithium

diethyl ether

(2R,4R)-1-(6-(6-ethanesulfonyl-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-4-hydroxy-pyrrolidin-2-carboxylic acid methoxy-methyl-amide

→

compound

1-((2R,4R)-1-(6-(6-ethanesulfonyl-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-4-hydroxy-pyrrolidin-2-yl)-ethanone

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타obtained in (step 1), at −78° C
2. 2
   기타The reaction liquid
3. 3
   온도heated up to 0° C.
4. 4
   workup.STIRRINGstirred for 1 hour
5. 5
   추출extracted with ethyl acetate
6. 6
   건조dried with anhydrous magnesium sulfate
7. 7
   기타The solvent was evaporated away under reduced pressure
8. 8
   기타the resulting residue was purified
9. 9
   기타through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

실험 절차

0.360 ml of methyl lithium (1.0 M diethyl ether solution was added to a tetrahydrofuran (1 ml) solution of 20 mg of (2R,4R)-1-(6-(6-ethanesulfonyl-pyridin-3-yloxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-4-hydroxy-pyrrolidin-2-carboxylic acid methoxy-methyl-amide obtained in (step 1), at −78° C. The reaction liquid was stirred at −78° C. for 1 hour, heated up to 0° C. and stirred for 1 hour. Aqueous saturated ammonium chloride solution was added to the reaction liquid, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a pale yellow solid.

출처