Tetrabutylammonium Fluoride → HCID 178469378, compound

HRID 571721Notes

Reaction equation

HRID 571721 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-b5e03febe79d4ab9abdf793e71ff68b5
Source dataset
uspto-grants-2015_05
Patent number
US09029366B2

Reaction notes

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