Hydrogen Peroxide → 2-{3-[2-(3-Methanesulfinyl-phenyl)-ethoxy]-4-methoxy-benzoylamino}-indane-2-carboxylic acid

HRID 521444Notes

Reaction equation

HRID 521444 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([C:7]([NH:9][C:10]2([C:19]([OH:21])=[O:20])[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[O:8])=[CH:5][C:4]=1[O:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([S:33][CH3:34])[CH:28]=1.[OH:35]O>C(O)(=O)C.O>[CH3:34][S:33]([C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][O:24][C:4]2[CH:5]=[C:6]([CH:22]=[CH:23][C:3]=2[O:2][CH3:1])[C:7]([NH:9][C:10]2([C:19]([OH:21])=[O:20])[CH2:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:18]2)=[O:8])[CH:32]=[CH:31][CH:30]=1)=[O:35]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 670767342-{4-Methoxy-3-[2-(3-methylsulfanyl-phenyl)-ethoxy]-benzoylamino}-indane-2-carboxylic acid

Product 1

HCID 670766222-{3-[2-(3-Methanesulfinyl-phenyl)-ethoxy]-4-methoxy-benzoylamino}-indane-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The compound of example 16 (35 mg, 0.078 mmol) was dissolved in acetic acid (2.5 ml), hydrogen peroxide (43 mg of a 30% solution in water, 0.38 mmol) was added and the mixture was stirred at room temperature for 2 h. The mixture was partitioned between EA and a 1% aqueous sodium sulfite solution, the aqueous phase extracted with EA, and the combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness to give 36 mg of the title compound.

Workup

  1. customThe mixture was partitioned between EA
  2. extractiona 1% aqueous sodium sulfite solution, the aqueous phase extracted with EA
  3. dry with materialthe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d5924dcc0a56470086fb61a65eba5273
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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