Ethyl Acetate → HCID 66839506, compound

HRID 546680Notes

Reaction equation

HRID 546680 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:36][CH2:37][CH2:38][CH:39]([CH3:59])[CH:40]([C:52]1[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=1)[C:41]([NH:43][NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:42])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.[Cl-].[NH4+]>C1COCC1>[F:58][C:55]1[CH:54]=[CH:53][C:52]([CH:40]([CH:39]([CH3:59])[CH2:38][CH2:37][OH:36])[C:41]([NH:43][NH:44][C:45]([O:47][C:48]([CH3:49])([CH3:51])[CH3:50])=[O:46])=[O:42])=[CH:57][CH:56]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 66839405HCID 66839405, compound

Product 1

HCID 66839506HCID 66839506, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (2.7 mL; 1 M solution in THF) was added to a solution of tert-butyl N′-[5-(tert-butyldiphenylsilanyloxy)-2-(4-fluorophenyl)-3-methylpentanoyl]hydrazinecarboxylate (1.04 g) in THF (20 mL). The reaction solution was stirred at room temperature for 1 hours. Then, ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 525 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-626d4923db0842498002bbeaeb9f2108
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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