Tetrabutylammonium Fluoride → HCID 178505099, compound

HRID 705357Notes

Reaction equation

HRID 705357 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([S:37]([CH3:40])(=[O:39])=[O:38])[C:14]1[C:33]([CH:34]2[CH2:36][CH2:35]2)=[CH:32][C:17]2[C:18]([C:28](=[N:30][OH:31])[NH2:29])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[O:20][C:16]=2[CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:34]1([C:33]2[C:14]([N:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[S:37]([CH3:40])(=[O:38])=[O:39])=[CH:15][C:16]3[O:20][C:19]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)=[C:18]([C:28](=[NH:29])[NH:30][OH:31])[C:17]=3[CH:32]=2)[CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317336856-[(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)(methylsulfonyl)amino]-5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-1-benzofuran-3-carboximidamide

Product 1

HCID 178505099HCID 178505099, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Example 16B (0.760 g, 1.289 mmol) in tetrahydrofuran (12 mL) was added 1 M tetrabutylammonium fluoride in tetrahydrofuran (3.22 mL, 3.22 mmol) in a fast drip, and the resulting yellow solution was stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was further washed with ethyl acetate (2×). The combined organic extracts were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to a clear oil that crystallized upon standing. Trituration with 1:2 v/v dichloromethane/hexane afforded the title compound as a white powder (0.588 g, 92%). MS (ESI+) m/z 476 (M+H)+, (ESI−) m/z 474 (M−H)−.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe aqueous layer was further washed with ethyl acetate (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a clear oil that
  7. customcrystallized

Sources & evidence

ORD record
ord-e2b3093a16ab4cf4a93df83d1420b03a
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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