Tetrabutylammonium Fluoride → HCID 178469378, compound

HRID 1396501Notes

Reaction equation

HRID 1396501 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][N:29]1[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:32][C:31]([O:39][Si](C(C)(C)C)(C)C)=[N:30]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1.O>[C:19]([O:23][C:24]([NH:26][CH2:27][CH2:28][N:29]1[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:32][C:31]([OH:39])=[N:30]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86706487ethyl 1-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-{[tert-butyl(dimethyl)silyl]oxy}-1H-pyrazole-5-carboxylate

Product 1

HCID 178469378HCID 178469378, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 1 M solution of tetrabutylammonium fluoride in THF (20.1 mL, 20.1 mmol) was added to a stirred solution of ethyl 1-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-{[tert-butyl(dimethyl)silyl]oxy}-1H-pyrazole-5-carboxylate (5.54 g, 13.4 mmol) in THF (45 mL). The mixture was stirred at room temperature for 16 hours, diluted with water and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield ethyl 1-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-hydroxy-1H-pyrazole-5-carboxylate (3.32 g, 83% yield) as a white solid, that was used in the next step without further purification.

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-3db36c3d6a51490981d3630a263ab9cd
Source dataset
uspto-grants-2014_12
Patent number
US08901125B2

Reaction notes

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