Réaction #41664

Équation de réaction

nitric acid

N-(4-(3-((t-butyl(dimethyl)silyl)oxy)pyrrolidin-2-yl)-3-fluorophenyl)pyridine-2-carboxamide

→

1-acetyl-2-(2-fluoro-5-nitro-4-((pyridin-2-ylcarbonyl)amino)phenyl)pyrrolidin-3-yl acetate

Conditions de réaction

Traitement

1. 1
   Autrethe reaction liquid
2. 2
   AutreThe reaction liquid
3. 3
   workup.ADDITIONwas poured into a mixed solution of ice-aqueous saturated sodium bicarbonate
4. 4
   Extractionextracted with chloroform
5. 5
   Séchagedried with anhydrous sodium sulfate
6. 6
   AutreThe solvent was evaporated away under reduced pressure
7. 7
   Autrethe resulting residue was purified
8. 8
   Autrethrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1)
9. 9
   Autreto obtain diastereomer A and diastereomer B of the entitled compound each as a yellow oily substance

Mode opératoire

1 ml of fuming nitric acid was added to 57 mg of N-(4-(3-((t-butyl(dimethyl)silyl)oxy)pyrrolidin-2-yl)-3-fluorophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at room temperature for 40 minutes. The reaction liquid was poured into a mixed solution of ice-aqueous saturated sodium bicarbonate, extracted with chloroform, and dried with anhydrous sodium 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=20/1) to obtain diastereomer A and diastereomer B of the entitled compound each as a yellow oily substance.

Source