Water → HCID 20792186, compound

HRID 2103114Notes

Reaction equation

HRID 2103114 reaction equation
[CH2:1]([S:5]([N:8](S(CCCC)(=O)=O)[C:9]1[CH:29]=[CH:28][C:12]2[O:13][C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:15][C:11]=2[CH:10]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[C:22]1([C:14]2([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:13][C:12]3[CH:28]=[CH:29][C:9]([NH:8][S:5]([CH2:1][CH2:2][CH2:3][CH3:4])(=[O:6])=[O:7])=[CH:10][C:11]=3[O:15]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 22475032HCID 22475032, compound

Product 1

HCID 20792186HCID 20792186, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N,N-Bis(butylsulfonyl)-2,2-diphenyl-1,3-benzodioxol-5-amine (Example 80, 79 mg, 0.15 mmol) was dissolved in tetrahydrofuran (4 ml). Tetrabutylammonium fluoride solution in tetrahydrofuran (1M, 0.16 mL, 0.16 mmol) was added dropwise at room temperature and the solution was stirred at room temperature overnight. The reaction was heated to reflux for 30 minutes, poured into water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated in vacuo. The residue was purified by column chromatography using dichloromethane as the eluant. Crystallization from hexane yielded the product as white crystals (45 mg, 74%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 30 minutes
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by column chromatography
  9. customCrystallization from hexane

Sources & evidence

ORD record
ord-6a7a5888bd8f426db411a3f14948eaff
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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