Tetrabutylammonium Fluoride → HCID 68093039, compound

HRID 1778413Notes

Reaction equation

HRID 1778413 reaction equation
[C:1]([O:5][C:6]([N:8]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([OH:19])[C:12]([C:20]2[C:24]([F:25])=[C:23]([Si](C)(C)C)[O:22][C:21]=2[CH2:30][O:31][Si](C(C)(C)C)(C)C)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([OH:19])[C:12]([C:20]2[C:24]([F:25])=[CH:23][O:22][C:21]=2[CH2:30][OH:31])=[CH:11][CH:10]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89558157HCID 89558157, compound2×

Product 1

HCID 68093039HCID 68093039, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 6-bis-(tert-butoxycarbonyl)amino-3-[2-(-tert-butyldimethylsilanyloxymethyl)-4-fluoro-5-trimethylsilanylfuran-3-yl]-2-hydroxybenzoate (Intermediate 100, 3.66 g) in a 1M solution of tetrabutylammonium fluoride in THF (30 mL) was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate and washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 10-50% to give methyl 6-bis-(tert-butoxycarbonyl)amino-3-(4-fluoro-2-hydroxymethylfuran-3-yl)-2-hydroxybenzoate (2.08 g) as a white solid.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 10-50%

Sources & evidence

ORD record
ord-56520afbb98347c8b0a36b1ef5c5565c
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

Loading…