Tetrabutylammonium Fluoride → HCID 18788115, compound

HRID 1106936Notes

Reaction equation

HRID 1106936 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C:27]([NH:29][CH2:30][C:31]([N:33]([CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][CH2:41][CH2:42][O:43][Si](C(C)(C)C)(C)C)=[O:32])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.C(OCC)(=O)C>[CH2:19]([O:26][C:27]([NH:29][CH2:30][C:31]([N:33]([CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][CH2:41][CH2:42][OH:43])=[O:32])=[O:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18788174HCID 18788174, compound

Product 1

HCID 18788115HCID 18788115, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (1.0M in THF/10 ml, 10 mmol) was added to a solution of N-(benzyloxycarbonylaminomethylcarbonyl)-N-(tert-butyloxycarbonyl-methyl)-2-(3-tert-butyldimethylsilyloxypropyl)aniline(3.87 g, 6.8 mmol) in THF (25 ml) at room temperature. After stirring for 90 minutes the reaction mixture was diluted with ethyl acetate (150 ml), washed with water (150 ml), brine (150 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by flash chromatography on silica gel with ethyl acetate-hexane (2:1) as eluant (2.39 g, 77%).

Workup

  1. washwashed with water (150 ml), brine (150 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-1d8a88bf1a7b438eb39733ba1c68688a
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

Loading…