Hydrogen Peroxide → HCID 67076254, compound

HRID 521436Notes

Reaction equation

HRID 521436 reaction equation
[CH3:1][S: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:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=1.[OH:34]O>C(O)(=O)C.O>[CH3:1][S:2]([C:3]1[CH:23]=[CH:22][C:6]([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:5][C:4]=1[O:24][CH2:25][CH2:26][C:27]1[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=1)=[O:34]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 44462759HCID 44462759, compound

Product 1

HCID 67076254HCID 67076254, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The compound of example 4 (100 mg, 0.216 mmol) was dissolved in acetic acid (7.5 ml), hydrogen peroxide (74 mg of a 30% solution in water, 0.65 mmol) was added, and the mixture was reacted at room temperature for 9 h. The mixture was partitioned between EA and a 1% aqueous sodium sulfite solution, the aqueous phase extracted with EA, and the organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was stirred with diethyl ether, filtered, and dried in vacuo to give 79 mg of the title compound.

Workup

  1. customthe mixture was reacted at room temperature for 9 h
  2. customThe mixture was partitioned between EA
  3. extractiona 1% aqueous sodium sulfite solution, the aqueous phase extracted with EA
  4. dry with materialthe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b774340966114ef6a8388ac9f6191b27
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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