Hydrogen Peroxide → HCID 23634286, compound

HRID 1810689Notes

Reaction equation

HRID 1810689 reaction equation
[OH:1]O.[CH3:3][C:4]1[CH:14]=[C:13]([O:15][CH2:16]/[CH:17]=[C:18](/[C:33]2[CH:38]=[CH:37][C:36]([S:39][CH3:40])=[CH:35][CH:34]=2)\[C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][N:28]3[CH:32]=[CH:31][CH:30]=[N: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>[CH3:40][S:39]([C:36]1[CH:35]=[CH:34][C:33](/[C:18](/[C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27][N:28]3[CH:32]=[CH:31][CH:30]=[N:29]3)=[CH:21][CH:20]=2)=[CH:17]/[CH2:16][O:15][C:13]2[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH3:3])[CH:14]=2)=[CH:38][CH:37]=1)=[O:1]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 23634212HCID 23634212, compound

Product 1

HCID 23634286HCID 23634286, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

30% Aqueous hydrogen peroxide (0.0618 mL, 0.6 mmol) was added to a solution of (E)-[4-[3-[4-(methylsulfanyl)phenyl]-3-[4-[3-(pyrazol-1-yl)propynyl]phenyl]allyloxy]-2-methylphenoxy]acetic acid (262 mg, 0.5 mmol; example 48) 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 (40 mL) and extracted with ethyl acetate (2×20 mL). The combined extracts were alkalized with 15% aqueous solution of ammonium hydroxide; the solution was washed with water (10 mL) and brine (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 (2×20 mL)
  4. washthe solution was washed with water (10 mL) and brine (10 mL)
  5. dry with materialdried with anhydrous magnesium sulphate
  6. customevaporated in vacuo
  7. customThe residue was triturated with hexanes (3×15 mL)

Sources & evidence

ORD record
ord-26352af2e0904983a7765aa0ff1de9ca
Source dataset
uspto-grants-2013_01
Patent number
US08362016B2

Reaction notes

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