Tetrabutylammonium Fluoride → HCID 66816812, compound

HRID 1754942Notes

Reaction equation

HRID 1754942 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][CH2:25][CH2:26][O:27][C:28]1[C:29]([CH3:61])=[C:30](/[CH:34]=[CH:35]/[S:36]([N:39]2[CH2:60][CH2:59][C:42]3([N:46]=[C:45]([C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([O:53][C:54]([F:57])([F:56])[F:55])[CH:48]=4)[NH:44][C:43]3=[O:58])[CH2:41][CH2:40]2)(=[O:38])=[O:37])[CH:31]=[CH:32][CH:33]=1)(C)(C)C>C1COCC1>[OH:24][CH2:25][CH2:26][O:27][C:28]1[C:29]([CH3:61])=[C:30](/[CH:34]=[CH:35]/[S:36]([N:39]2[CH2:40][CH2:41][C:42]3([N:46]=[C:45]([C:47]4[CH:52]=[CH:51][CH:50]=[C:49]([O:53][C:54]([F:56])([F:57])[F:55])[CH:48]=4)[NH:44][C:43]3=[O:58])[CH2:59][CH2:60]2)(=[O:37])=[O:38])[CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66818324HCID 66818324, compound

Product 1

HCID 66816812HCID 66816812, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (0.11 ml, 0.11 mmol, 1 M in THF) was added to a solution of 8-((E)-2-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-2-methyl-phenyl}-ethenesulfonyl)-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one obtained above in anhydrous THF (1 ml) at room temperature in an Ar atmosphere. The mixture was stirred at room temperature for two hours and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:EtOAc=1:1) to give 8-{(E)-2-[3-(2-hydroxy-ethoxy)-2-methyl-phenyl]-ethenesulfonyl}-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (3.2 mg, yield in two steps: 48%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-a8d66b3b1c204f4d9ed2ca89c4e81d97
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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