Tetrabutylammonium Fluoride → HCID 59347369, compound

HRID 2366551Notes

Reaction equation

HRID 2366551 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][N:31]([CH:35]2[CH2:40][CH2:39][N:38]([C:41](=[O:59])[C@H:42]([OH:58])[CH2:43][S:44]([C:47]3[CH:56]=[CH:55][C:54]4[C:49](=[CH:50][CH:51]=[C:52]([Cl:57])[CH:53]=4)[CH:48]=3)(=[O:46])=[O:45])[CH2:37][CH2:36]2)[C:30]1=[O:60])(C(C)(C)C)(C)C>C1COCC1>[Cl:57][C:52]1[CH:53]=[C:54]2[C:49](=[CH:50][CH:51]=1)[CH:48]=[C:47]([S:44]([CH2:43][C@@H:42]([OH:58])[C:41]([N:38]1[CH2:37][CH2:36][CH:35]([N:31]3[CH2:32][CH2:33][CH2:34][N:29]([CH2:28][CH2:27][OH:26])[C:30]3=[O:60])[CH2:40][CH2:39]1)=[O:59])(=[O:45])=[O:46])[CH:56]=[CH:55]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59347365HCID 59347365, compound

Product 1

HCID 59347369HCID 59347369, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (0.12 g) was added to a solution of 1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(1-{(2S)-3-[(6-chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl}piperidin-4-yl)tetrahydropyrimidin-2(1H)-one (0.25 g) obtained in Example 40c) in THF (10 mL), and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with an aqueous 5% citric acid solution and saturated saline solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=95/5 to ethyl acetate/methanol=90/10) to obtain the title compound (0.11 g, 54%) as a white powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe mixture was washed with an aqueous 5% citric acid solution and saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=95/5 to ethyl acetate/methanol=90/10)

Sources & evidence

ORD record
ord-d5c3c85f905248998884cbf5605ccf05
Source dataset
uspto-grants-2014_04
Patent number
US08697865B2

Reaction notes

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