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Hydroxyamine hydrochloride → tert-butyl {[5-{2-fluoro-3-[(hydroxyimino)methyl]phenyl}-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 1782354
Notes
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Reaction equation

HRID 1782354 reaction equation
[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[C:16]=2[F:23])[N:12]([S:24]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)(=[O:26])=[O:25])[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:35][OH:36].C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>CC(O)C>[F:23][C:16]1[C:17]([CH:21]=[N:35][OH:36])=[CH:18][CH:19]=[CH:20][C:15]=1[C:13]1[N:12]([S:24]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)(=[O:26])=[O:25])[CH:11]=[C:10]([CH2:9][N:7]([CH3:8])[C:6](=[O:33])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 86631002tert-butyl {[5-(2-fluoro-3-formylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Product 1

HCID 86631005tert-butyl {[5-{2-fluoro-3-[(hydroxyimino)methyl]phenyl}-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate
Yield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution (3 mL) of tert-butyl{[5-(2-fluoro-3-formylphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (182 mg) in 2-propanol were added hydroxylamine hydrochloride (40 mg) and sodium acetate (47 mg). After stirring at room temperature for 3 hr, saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1) to give the title compound as a pale-yellow oil (yield 150 mg, 80%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1)

Sources & evidence

ORD record
ord-aebfa6072d1a4614bf68fd306315f268
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07498337B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes