Water → Agn-PC-0MW2M5

HRID 1635936Notes

Reaction equation

HRID 1635936 reaction equation
S([CH2:11][N+:12]#[C-:13])(C1C=CC(C)=CC=1)(=O)=O.[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[K+].O.[CH2:21]([O:23][C:24](=[O:26])[CH3:25])[CH3:22].[CH3:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O1CCC[CH2:34]1>>[C:15]1([C:18]2[C:25]([C:24]([O:23][CH2:21][CH3:22])=[O:26])=[CH:11][NH:12][CH:13]=2)[C:16]2[C:29](=[CH:30][CH:31]=[CH:32][CH:34]=2)[CH:28]=[CH:27][CH:14]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 161915Tosylmethyl isocyanideHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 9943237Agn-PC-0MW2M5Yield 77%

Procedure

5 g(18.9 mmol) of the compound prepared in Preparation 1-1) and 3.68 g(18.9 mmol) of tosylmethylisocyanide were dissolved in 100 ml of tetrahydrofuran. 2.55 g(22.7 mmol) of potassium t-butoxide dissolved in 100 ml of tetrahydrofuran was slowly added thereto and the resulting mixture was refluxed for 30 minutes. 100 ml of water was added to the reaction solution to stop the reaction and the solvent was removed under reduced pressure. The residue was extracted with diethylether, washed with saturated sodium chloride solution and dried over magnesium sulfate. Then, the solvent was removed under reduced pressure and the residue was subjected to column chromatography(eluent: ethylacetate/n-hexane=⅓, v/v) to give 3.85 g(14.5 mmol, Yield 77%) of the title compound.

Workup

  1. additionwas slowly added
  2. temperaturethe resulting mixture was refluxed for 30 minutes
  3. customthe reaction
  4. customthe solvent was removed under reduced pressure
  5. extractionThe residue was extracted with diethylether
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThen, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-248ccb57a903429fb3282073a2927f72
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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