Hydrogen Peroxide → HCID 86700816, compound

HRID 2406551Notes

Reaction equation

HRID 2406551 reaction equation
[OH:1]O.[C:3]([C:5]1[C:6]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][CH:30]=2)=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([O:14][C:15]1[CH:27]=[CH:26][C:18]3[C@H:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:20][O:21][C:17]=3[CH:16]=1)[CH2:9][CH2:8]2)#[N:4]>FC(F)(F)C(O)C(F)(F)F.C(OCC)(=O)C>[C:3]([C:5]1[C:6]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([S:35]([CH3:36])=[O:1])=[CH:33][CH:34]=2)=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([O:14][C:15]1[CH:27]=[CH:26][C:18]3[C@H:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:20][O:21][C:17]=3[CH:16]=1)[CH2:9][CH2:8]2)#[N:4]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 72203514HCID 72203514, compound

Product 1

HCID 86700816HCID 86700816, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

Aqueous hydrogen peroxide (35%, 5 μL) is added to a solution of {(S)-6-[(R)-5-cyano-4-(4-methylsulfanyl-benzyl)-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid (120 mg) in 1,1,1,3,3,3-hexafluoro-2-propanol (1.5 mL) at room temperature. The mixture is stirred at room temperature for 2 h and then diluted with ethyl acetate. The resulting mixture is washed with aqueous Na2S2C3 solution, 1 M aqueous HCl solution, and brine, and dried (Na2SO4). The solvent is evaporated to give the title compound. LC (method 4): tR=0.98 min; Mass spectrum (ESI+): m/z=488 [M+H]+.

Workup

  1. washThe resulting mixture is washed with aqueous Na2S2C3 solution, 1 M aqueous HCl solution, and brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-6e28bb8e1dc84da3a40b1e365b40cf96
Source dataset
uspto-grants-2014_08
Patent number
US08809376B2

Reaction notes

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