Tetrahydrofuran → HCID 86661494, compound

HRID 1626765Notes

Reaction equation

HRID 1626765 reaction equation
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[CH:27]1([C:33]2[CH:38]=[CH:37][C:36]([C:39]([NH:41][C:42]3[CH:51]=[CH:50][C:49]([C:52]#[C:53][Si](C)(C)C)=[CH:48][C:43]=3[C:44]([O:46][CH3:47])=[O:45])=[O:40])=[CH:35][CH:34]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(OCC)(=O)C>[CH:27]1([C:33]2[CH:34]=[CH:35][C:36]([C:39]([NH:41][C:42]3[CH:51]=[CH:50][C:49]([C:52]#[CH:53])=[CH:48][C:43]=3[C:44]([O:46][CH3:47])=[O:45])=[O:40])=[CH:37][CH:38]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 66680839HCID 66680839, compound

Product 1

HCID 86661494HCID 86661494, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

351 mg (1.1 mmol) of tetrabutyl ammonium fluoride trihydrate was added to a THF (9 mL) solution comprising 322 mg (0.74 mmol) of methyl 2-{[(4-cyclohexylphenyl)carbonyl]amino}-5-[(trimethylsilyl)ethynyl]benzoate at 0° C., and the mixture was stirred for 1.5 hours. Thereafter, the reaction mixture was diluted with ethyl acetate, and washed with saturated saline. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 208 mg of methyl 2-{[(4-cyclohexylphenyl)carbonyl]amino}-5-ethynylbenzoate (yield: 78%).

Workup

  1. washwashed with saturated saline
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained crude product
  5. customwas separated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-f4a4d2cd959f4fc5ae0379ce9c39e473
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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