تفاعل #41649

معادلة التفاعل

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

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر