Tetrabutylammonium Fluoride → HCID 56603201, compound

HRID 1802443Notes

Reaction equation

HRID 1802443 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][C:8]([C:11]1[CH:15]=[C:14]([NH:16][C:17](=[O:32])[C:18]([CH3:31])([S:20]([CH2:23][CH:24]2[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]2)(=[O:22])=[O:21])[CH3:19])[O:13][N:12]=1)([CH3:10])[CH3:9])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][CH2:7][C:8]([C:11]1[CH:15]=[C:14]([NH:16][C:17](=[O:32])[C:18]([CH3:31])([S:20]([CH2:23][CH:24]2[CH2:25][CH2:26][C:27](=[O:30])[CH2:28][CH2:29]2)(=[O:22])=[O:21])[CH3:19])[O:13][N:12]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59268004HCID 59268004, compound

Product 1

HCID 56603201HCID 56603201, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.12 g (0.19 mmol) of N-{3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-isoxazol-5-yl}-2-methyl-2-(4-oxo-cyclohexylmethanesulfonyl)-propionamide in THF (2 mL) is added tetrabutylammonium fluoride (0.65 mL, 0.65 mmol, 1M solution in THF) and the reaction is stirred at room temperature for 48 h. The reaction mixture is quenched by addition of saturated aqueous NH4Cl solution (5 mL) and the mixture is extracted with DCM (8 mL×3). The combined organic extracts are washed with brine (10 mL), dried (MgSO4) and filtered. The filtrate is concentrated under reduced pressure and the residue purified twice by column chromatography (silica, eluent: DCM, 20% ethyl acetate, then DCM, 10% ethyl acetate) to afford 0.03 g of N-[3-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-5-yl]-2-methyl-2-(4-oxo-cyclohexylmethanesulfonyl)-propionamide. Yield: 41%, ES-MS: 401 [M+H]

Workup

  1. customThe reaction mixture is quenched by addition of saturated aqueous NH4Cl solution (5 mL)
  2. extractionthe mixture is extracted with DCM (8 mL×3)
  3. washThe combined organic extracts are washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customthe residue purified twice by column chromatography (silica, eluent

Sources & evidence

ORD record
ord-3d8452b537b34c2d856cd05f1e3b34f1
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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