Water → 4-[N-(tert-butyl)-N-hydroxyamino]-N-pyridin-2-yl-methyl-benzamide

HRID 498085Notes

Reaction equation

HRID 498085 reaction equation
[C:1]([N:5]([C:14]1[CH:28]=[CH:27][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:19])=[C:16]([CH3:29])[CH:15]=1)[O:6][Si](C(C)(C)C)(C)C)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[C:1]([N:5]([C:14]1[CH:28]=[CH:27][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)=[O:19])=[C:16]([CH3:29])[CH:15]=1)[OH:6])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 22320694HCID 22320694, compound

Product 1

HCID 223207134-[N-(tert-butyl)-N-hydroxyamino]-N-pyridin-2-yl-methyl-benzamideYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.06 g (0.145 mmol) of compound 7 in THF (1 mL) was added 0.73 mL (0.73 mmol) of 1 M solution of tetrabutylammonium fluoride in THF at room temperature, and the solution was stirred for 24 hours. After completion of the reaction, 2 mL of water was added to quench the reaction. Ethyl acetate and sat'd NH4Cl solution were added to the mixture. The organic layer was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=1:2) to give 0.026 g of compound 8 in 60% yield.

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. additionwere added to the mixture
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=1:2)

Sources & evidence

ORD record
ord-fa7977408ca44cc4b3882470ee97ce12
Source dataset
uspto-grants-2005_09
Patent number
US06949654B2

Reaction notes

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