Tetrabutylammonium Fluoride → HCID 68897255, compound

HRID 1783673Notes

Reaction equation

HRID 1783673 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:13])=[CH:11][C:10]([N:14]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25](C)(C)[O:26][SiH2]C(C)(C)C)=[CH:22][CH:23]=3)[C:18](=[O:34])[N:17]([CH:35]([CH3:37])[CH3:36])[N:16]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:13])=[CH:11][C:10]([N:14]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[C:15]2[C:24]3[C:19](=[CH:20][C:21]([CH2:25][OH:26])=[CH:22][CH:23]=3)[C:18](=[O:34])[N:17]([CH:35]([CH3:36])[CH3:37])[N:16]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131726479HCID 131726479, compound

Product 1

HCID 68897255HCID 68897255, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-{tert-Butoxycarbonyl-[6-(tert-butyl-dimethyl-silanyloxymethyl)-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-1-yl]-amino}-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.78, 1.25 mmol) was dissolved in THF (3 ml), to this was added a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (1.87 ml, 1.87 mmol) and the mixture was stirred at RT for 24 hours. After this time the reaction mixture was concentrated under vacuum and the residue was purified by flash column chromatography (elution: 50% heptane, 50% EtOAc) to give the title compound (0.39 g, 45% yield) as a brown solid MS (ESI+)=(M+H)+ 514.43.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated under vacuum
  2. customthe residue was purified by flash column chromatography (elution: 50% heptane, 50% EtOAc)

Sources & evidence

ORD record
ord-f1a70e7a2be4443788607e2c2a0efd53
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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