Water → HCID 22320692, compound

HRID 498084Notes

Reaction equation

HRID 498084 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])=[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.C([O-])(O)=O.[Na+]>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])=[CH:16][CH:15]=1)[OH:6])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 22320676HCID 22320676, compound

Product 1

HCID 22320692HCID 22320692, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.95 g (2.37 mmol) of compound 5 in THF (3 mL) was added 2.84 mL (2.84 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 NaHCO3 solution were added to the mixture, and 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 0.44 g of compound 6 in 65% 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-97a09f27897e4f41907a7aeca41e545c
Source dataset
uspto-grants-2005_09
Patent number
US06949654B2

Reaction notes

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