Tetrabutylammonium Fluoride → HCID 135405285, compound

HRID 244267Notes

Reaction equation

HRID 244267 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 0.1%

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 mol), 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 (Ac0H-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 (Ac0H-EtOH, 20:1)

Sources & evidence

ORD record
ord-8cdf8d93c1554e41becb6947e85f967e
Source dataset
uspto-grants-2014_02
Patent number
USRE044779E1

Reaction notes

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