Hydrogen Peroxide → HCID 68542676, compound

HRID 1445722Notes

Reaction equation

HRID 1445722 reaction equation
[C:1]1([NH:7][C:8]([N:10]2[C@H:19]3[C:14]([C:15]4[CH:25]=[CH:24][CH:23]=[C:22]5[C:16]=4[C@@H:17]([CH2:20][NH:21]5)[CH2:18]3)=[CH:13][C@@H:12]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])[CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:33].OO>CO.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[C:1]1([NH:7][C:8]([N:10]2[C@H:19]3[C:14]([C:15]4[CH:25]=[CH:24][CH:23]=[C:22]5[C:16]=4[C:17](=[CH:20][N:21]5[OH:33])[CH2:18]3)=[CH:13][C@@H:12]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])[CH2:11]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 68543759HCID 68543759, compound

Product 1

HCID 68542676HCID 68542676, compound

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 887MethanolSolvent

Procedure

212 mg (0.49 mmol) of the product of step 1 is dissolved in 12 ml methanol and 41 mg (0.12 mmol, 0.25 eq.) sodium wolframate dehydrate in some drops of water is added. Then 670 μl 30% H2O2 (10 eq.) is added at 0° C. and stirred at room temperature for 50 minutes. The reaction mixture is separated with dichloromethane and saturated aqueous bicarbonate solution, the organic layer is washed with brine, dried with Na2SO4 and evaporated and purified by chromatography on silica eluting with tert. butyl methyl ether:cyclohexane 9:1 to give (6aR,9R)-4-Hydroxy-9-(pyrrolidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid phenylamide. MS/ES: 441 (M+H)+

Workup

  1. customThe reaction mixture is separated with dichloromethane and saturated aqueous bicarbonate solution
  2. washthe organic layer is washed with brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. custompurified by chromatography on silica eluting with tert. butyl methyl ether:cyclohexane 9:1

Sources & evidence

ORD record
ord-17d7944f48434b80b0f9c9844d228e9d
Source dataset
uspto-grants-2010_02
Patent number
US07666877B2

Reaction notes

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