Acetic Acid → HCID 178464145, compound

HRID 1170449Notes

Reaction equation

HRID 1170449 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([OH:35])[C:17]2[C:12](=[CH:13][C:14](SC)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:24][C@H:25]2[CH2:28][C@H:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:26]2)[C:10]1=[O:34].OO.[S:38]([O-:42])([O-])(=[O:40])=S.[Na+].[Na+].[C:45](O)(=O)C>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([OH:35])[C:17]2[C:12](=[CH:13][C:14]([S:38]([CH3:45])(=[O:42])=[O:40])=[CH:15][C:16]=2[C:18]([F:20])([F:21])[F:19])[N:11]([CH2:24][C@H:25]2[CH2:28][C@H:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:26]2)[C:10]1=[O:34]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 178464144HCID 178464144, compound

Product 1

HCID 178464145HCID 178464145, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 150191Sodium Tungstate DihydrateCatalyst

Procedure

To a solution of the compound of Example 32-1 (70 mg) in acetic acid (1 mL) were added sodium tungstate dihydrate (39 mg, 0.118 mmol) and 30% aqueous hydrogen peroxide (0.1 mL), and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate and washed with saturated saline, and the organic layer was dried over magnesium sulfate and filtered, and then the filtrate was evaporated and purified by silica gel column chromatography (chloroform/methanol=20/1 to 10/1) followed by hydrochloride salt formation to give the titled compound (29 mg, 31%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated saline
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated
  6. custompurified by silica gel column chromatography (chloroform/methanol=20/1 to 10/1)

Sources & evidence

ORD record
ord-f6e921c25bb54112bcc1adfd6b393aed
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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