Tetrabutylammonium Fluoride → HCID 135405285, compound

HRID 1835638Notes

Reaction equation

HRID 1835638 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C@@H:27]1[C@@:31]2([CH2:51][O:52][C@H:28]1[C@H:29]([N:53]1[C:68]3[N:67]=[C:60]([NH:61][C:62](=[O:66])[CH:63]([CH3:65])[CH3:64])[NH:59][C:57](=[O:58])[C:56]=3[N:55]=[CH:54]1)[O:30]2)[CH2:32][O:33][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:19]([O:26][C@@H:27]1[C@@:31]2([CH2:51][O:52][C@H:28]1[C@H:29]([N:53]1[C:68]3[N:67]=[C:60]([NH:61][C:62](=[O:66])[CH:63]([CH3:64])[CH3:65])[NH:59][C:57](=[O:58])[C:56]=3[N:55]=[CH:54]1)[O:30]2)[CH2:32][OH:33])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 136344205HCID 136344205, compound

Product 1

HCID 135405285HCID 135405285, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M in THF, 0.90 ml, 0.90 mmol) was added, at room temperature, to a tetrahydrofuran solution (3.0 ml) of Compound 46 (41.3 mg, 0.060 mmol), and the mixture was stirred for 1 hour at room temperature. The reaction mixture was distilled under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (AcOH-EtOH, 20:1) to obtain a white powder, Compound 47 (27.1 mg, 0.060 mmol, quant.).

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customthe resulting crude product was purified by silica gel column chromatography (AcOH-EtOH, 20:1)

Sources & evidence

ORD record
ord-77f297bb79434ac6b5d29a0225f576c6
Source dataset
uspto-grants-2004_08
Patent number
US06770748B2

Reaction notes

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