Nitric Acid → 1-Acetyl-2-(2-fluoro-5-nitro-4-((pyridin-2-ylcarbonyl)amino)phenyl)pyrrolidin-3-yl acetate
Reaction equation
[N+:1]([O-:4])(O)=[O:2].[Si]([O:12][CH:13]1[CH2:17][CH2:16][NH:15][CH:14]1[C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:26])=[CH:20][C:19]=1[F:33])(C(C)(C)C)(C)C>>[C:13]([O:12][CH:13]1[CH2:17][CH2:16][N:15]([C:25](=[O:26])[CH3:27])[CH:14]1[C:18]1[CH:23]=[C:22]([N+:1]([O-:4])=[O:2])[C:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:26])=[CH:20][C:19]=1[F:33])(=[O:12])[CH3:14]Participants
3
Procedure
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.
Workup
- customthe reaction liquid
- customThe reaction liquid
- additionwas poured into a mixed solution of ice-aqueous saturated sodium bicarbonate
- extractionextracted with chloroform
- dry with materialdried with anhydrous sodium sulfate
- customThe solvent was evaporated away under reduced pressure
- customthe resulting residue was purified
- customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1)
- customto obtain diastereomer A and diastereomer B of the entitled compound each as a yellow oily substance
Sources & evidence
- ORD record
- ord-2c848de35fda48d3a4611fde2acceabc
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728025B2
Reaction notes
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