Water → HCID 10154941, compound

HRID 498087Notes

Reaction equation

HRID 498087 reaction equation
[C:1]([N:5]([C:14]1[CH:33]=[CH:32][C:17]([C:18]([NH:20][C:21]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]3[C:22]=2[CH:23]=[CH:24][CH:25]=[N:26]3)=[O:19])=[CH:16][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:33]=[CH:32][C:17]([C:18]([NH:20][C:21]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]3[C:22]=2[CH:23]=[CH:24][CH:25]=[N:26]3)=[O:19])=[CH:16][CH:15]=1)[OH:6])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 223207184-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamide

Product 1

HCID 10154941HCID 10154941, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.04 g (0.085 mmol) of compound 9 in THF (1 mL) was added 0.43 mL (0.43 mmol) of 1 M solution of tetrabutylammonium fluoride in THF at room temperature, and the solution was stirred for 1 hour. 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=10:1) to give 0.021 g of compound 10 in 70% 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=10:1)

Sources & evidence

ORD record
ord-b56c13ee9d884a7aa4b70111b35216e5
Source dataset
uspto-grants-2005_09
Patent number
US06949654B2

Reaction notes

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