Tetrabutylammonium Fluoride → HCID 69221542, compound

HRID 132853Notes

Reaction equation

HRID 132853 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:12]([O:30][CH3:31])=[N:13][C:14]([C:26]([F:29])([F:28])[F:27])=[CH:15][C:16]=1[CH2:17][O:18][Si](C(C)(C)C)(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:12]([O:30][CH3:31])=[N:13][C:14]([C:26]([F:27])([F:28])[F:29])=[CH:15][C:16]=1[CH2:17][OH:18])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69224268HCID 69224268, compound

Product 1

HCID 69221542HCID 69221542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound from Step K above (1.12 g, 2.41 mmol) in tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride (11.0M in tetrahydrofuran, 2.41 mL, 2.41 mmol). The reaction was then stirred at room temperature for 10 min and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel; 20% to 40% ethyl acetate/hexanes gradient elution) to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.38 (s, 1H), 4.87 (br s, 1H), 4.76 (d, 2H, J=6 Hz), 4.02 (s, 3H), 3.54 (t, 1H), 3.35 (m, 2H), 2.88 (t, 2H, J=6 Hz), 1.38 (s, 9H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (silica gel; 20% to 40% ethyl acetate/hexanes gradient elution)

Sources & evidence

ORD record
ord-58482d8711b649ef85974358671decc7
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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