Hydrochloric Acid → HCID 59235015, compound

HRID 1919762Notes

Reaction equation

HRID 1919762 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:36][CH2:37][C:38]#[C:39][CH2:40][N:41]1[C:45](=[O:46])[C:44]([CH3:57])([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH:54]([CH3:56])[CH3:55])=[CH:49][CH:48]=2)[NH:43][C:42]1=[O:58])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>O1CCCC1>[OH:36][CH2:37][C:38]#[C:39][CH2:40][N:41]1[C:45](=[O:46])[C:44]([CH3:57])([C:47]2[CH:52]=[CH:51][C:50]([O:53][CH:54]([CH3:55])[CH3:56])=[CH:49][CH:48]=2)[NH:43][C:42]1=[O:58]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 59235122HCID 59235122, compound

Product 1

HCID 59235015HCID 59235015, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetrabutylammonium fluoride in tetrafuran (602 μL) was added to a mixed solution of 3-[4-(t-butyl-diphenylsilyloxy)-2-butynyl]-5-methyl-5-[4-(1-methylethoxy)phenyl]imidazolidine-2,4-dione (300 mg, 547 μmol) in tetrahydrofuran (5 mL) at room temperature. After completion of the reaction, 1 mol/L hydrochloric acid (0.5 mL) was added, followed by extraction with ethyl acetate-water. The organic layer was washed with a saturation sodium chloride solution and then dried over sodium sulfate. The solvent of the filtrate was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 115 mg of the title compound (yield: 90%) as a colorless oil.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate-water
  3. washThe organic layer was washed with a saturation sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent of the filtrate was evaporated
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-72ffae7d4df0451397a0f64746993936
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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