Hydrogen Peroxide → HCID 23634137, compound

HRID 549878Notes

Reaction equation

HRID 549878 reaction equation
[OH:1]O.[CH3:3][C:4]1[CH:14]=[C:13]([O:15][CH2:16]/[CH:17]=[C:18](/[C:34]2[CH:39]=[CH:38][C:37]([S:40][CH3:41])=[CH:36][CH:35]=2)\[C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=2)[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9]>C(O)(=O)C.O>[CH3:3][C:4]1[CH:14]=[C:13]([O:15][CH2:16]/[CH:17]=[C:18](/[C:34]2[CH:35]=[CH:36][C:37]([S:40]([CH3:41])=[O:1])=[CH:38][CH:39]=2)\[C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=2)[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 23634136HCID 23634136, compound

Product 1

HCID 23634137HCID 23634137, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

30% Aqueous hydrogen peroxide (0.0613 mL, 0.6 mmol) was added to a solution of (E)-[2-methyl-4-[3-(4-methylsulfanylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]-allyloxy]-phenoxy]acetic acid (272 mg, 0.5 mmol; example 40) in glacial acetic acid (7 mL) at 5° C. under stirring. The mixture was left to stand over night at ambient temperature, diluted with water and extracted with ethyl acetate (2×30 mL). The collected extracts were alkalized with 15% solution of ammonium hydroxide; the solution was decanted from the separated oil and the oil was and dissolved in chloroform (45 mL). The solution was washed with water (2×10 mL), dried with anhydrous magnesium sulphate and evaporated in vacuo. The residue was triturated with hexanes (3×15 mL) to yield the title compound as pale solid.

Workup

  1. waitThe mixture was left
  2. waitto stand over night at ambient temperature
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. customthe solution was decanted from the separated oil
  5. dissolutiondissolved in chloroform (45 mL)
  6. washThe solution was washed with water (2×10 mL)
  7. dry with materialdried with anhydrous magnesium sulphate
  8. customevaporated in vacuo
  9. customThe residue was triturated with hexanes (3×15 mL)

Sources & evidence

ORD record
ord-0f64bed54b304a7e9ad34437277d52f8
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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