Water → HCID 66960849, compound

HRID 1362636Notes

Reaction equation

HRID 1362636 reaction equation
C1COCC1.[C:6]([O:10][C:11](=[O:38])/[C:12](=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]2)=[C:26]([O:36][CH3:37])[CH:25]=1)/[CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)([CH3:9])([CH3:8])[CH3:7].CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C(OCC)(=O)C>[C:6]([O:10][C:11](=[O:38])/[C:12](=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]2)=[C:26]([O:36][CH3:37])[CH:25]=1)/[CH2:13][CH2:14][OH:15])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 66960947HCID 66960947, compound

Product 1

HCID 66960849HCID 66960849, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a THF (10 mL) solution of (E)-4-(tert-butyldimethylsilanyloxy)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)butyric acid tert-butyl ester (122 mg), TBAF (1M THF solution, 318 μL) was added, and the reaction solution was agitated at room temperature for 1 hour. After confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:ethanol=10:1), and 49.7 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. additionwere added to the reaction solution
  2. customthe organic layer was partitioned
  3. washAfter the obtained organic layer was washed with a saturated saline solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-5f348cf3da4644a995b5a89d11ebd42e
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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