Tetrabutylammonium Fluoride → Rac-[1-(4-chloro-phenyl)-2-(4-hydroxy-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

HRID 384905Notes

Reaction equation

HRID 384905 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH:8]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][Si](C(C)(C)C)(C)C)=[CH:13][CH:12]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CO.O1CCCC1.C(OCC)C>[C:1]([O:5][C:6](=[O:32])[NH:7][CH:8]([C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68412036Rac-[2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(4-chloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68409176Rac-[1-(4-chloro-phenyl)-2-(4-hydroxy-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.37 g (2.88 mmol) rac-[2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-(4-chloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester in 30 ml methanol were added at ambient temperature 3.45 ml (3.45 mmol) 1M tetrabutylammonium fluoride in tetrahydrofuran. After 10 min the reaction mixture was diluted with diethyl ether, the solution washed twice with sodium bicarbonate solution and once with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash-chromatography over silica gel with a heptane/ethyl acetate gradient of 0 to 80% ethyl acetate. The purified title compound was triturated in di-isopropyl ether, filtered, dried and obtained as colorless solid: MS (ISN): 360.2 (M−H)−.

Workup

  1. washthe solution washed twice with sodium bicarbonate solution and once with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash-chromatography over silica gel with a heptane/ethyl acetate gradient of 0 to 80% ethyl acetate
  6. customThe purified title compound
  7. customwas triturated in di-isopropyl ether
  8. filtrationfiltered
  9. customdried
  10. customobtained as colorless solid

Sources & evidence

ORD record
ord-de6466c77a4a454b89df525917247d52
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

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