Tetrabutylammonium Fluoride → HCID 69919337, compound

HRID 2307821Notes

Reaction equation

HRID 2307821 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([O:23][CH:24]([C:34](C)(C)[O:35][SiH2]C(C)(C)C)[CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:22]=3)=[CH:14][CH:15]=2)[C:10]([CH3:43])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([O:23][CH:24]([CH2:34][OH:35])[CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:22]=3)=[CH:14][CH:15]=2)[C:10]([CH3:43])=[N:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178434140HCID 178434140, compound

Product 1

HCID 69919337HCID 69919337, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 393C (1.122 g, 1.83 mmol) in THF (20 mL) was added TBAF (1.92 mL) at rt. The solution was stirred at rt for 1 h and was concentrated. The residual oil was separated by flash chromatography (0-15% CH3OH in 2:1 EtOAc/hexane) to give the title compound (0.82 g, 90%). MS (DCI) m/z 499 (M+1)+.

Workup

  1. concentrationwas concentrated
  2. customThe residual oil was separated by flash chromatography (0-15% CH3OH in 2:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-63cc46849a5e4eeeb2f08bebeac42383
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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