Tetrabutylammonium Fluoride → HCID 86707800, compound

HRID 2174393Notes

Reaction equation

HRID 2174393 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]1([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH2:44][C:43]([C:49]4[CH:54]=[C:53]([Cl:55])[C:52]([Cl:56])=[C:51]([Cl:57])[CH:50]=4)([C:45]([F:48])([F:47])[F:46])[O:42][N:41]=3)=[CH:36][CH:35]=2)[CH2:23][CH:22]([NH:24]C(=O)OCC[Si](C)(C)C)[CH2:21]1>C1COCC1>[F:19][C:20]1([C:34]2[CH:35]=[CH:36][C:37]([C:40]3[CH2:44][C:43]([C:49]4[CH:54]=[C:53]([Cl:55])[C:52]([Cl:56])=[C:51]([Cl:57])[CH:50]=4)([C:45]([F:46])([F:47])[F:48])[O:42][N:41]=3)=[CH:38][CH:39]=2)[CH2:23][CH:22]([NH2:24])[CH2:21]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707799HCID 86707799, compound

Product 1

HCID 86707800HCID 86707800, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 M TBAF in THF (576 μL, 0.576 mmol) is added to a mixture of 2-(trimethylsilyl)ethyl (3-fluoro-3-(4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)cyclobutyl)carbamate (Preparation 15, 120.0 mg, 0.19 mmol) in THF (1.9 mL). After stirring overnight, the reaction mixture is partitioned between EtOAc (5 mL) and brine (5 mL), the organics were separated, dried over MgSO4 and filtered to give an oil which was further purified using regular silica eluting from neat heptane to neat EtOAc to give the title compound (100 mg): m/z (Cl) 480.

Workup

  1. customthe reaction mixture is partitioned between EtOAc (5 mL) and brine (5 mL)
  2. customthe organics were separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customto give an oil which
  6. customwas further purified

Sources & evidence

ORD record
ord-49ac096ab95a4d348af32182df6a0bd4
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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