HCID 19348362, compound → HCID 19348296, compound

HRID 1637279Notes

Reaction equation

HRID 1637279 reaction equation
[NH2:1][CH:2]1[CH2:19][CH:6]2[CH:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:4]([C:5]=32)[CH2:3]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[NH2:1][CH:2]1[CH2:19][C:6]2=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:4]([C:5]=32)[CH2:3]1

Participants

4

Reactant 1

HCID 19348362HCID 19348362, compound

Product 1

HCID 19348296HCID 19348296, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A portion (0.83 g) of the compound obtained in Example 166 was dissolved in methylene chloride (80 ml) and to the solution was added active manganese dioxide (1.66 g). The mixture was heated to reflux for 28 hours. The manganese dioxide was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=7:1) to yield 240 mg (29%) of the titled compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 28 hours
  3. filtrationThe manganese dioxide was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=7:1)

Sources & evidence

ORD record
ord-c554c47d6e2a46e6834bbc6c742e793e
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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