Tetrabutylammonium Fluoride → HCID 68897255, compound

HRID 1765359Notes

Reaction equation

HRID 1765359 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>O1CCCC1>[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 tetrahydrofuran (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 room temperature 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% ethyl acetate) 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% ethyl acetate)

Sources & evidence

ORD record
ord-c3b9c9da302d477c9f32b37e2f0d8cd1
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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