HCID 19348119, compound → HCID 19348289, compound

HRID 1637275Notes

Reaction equation

HRID 1637275 reaction equation
[CH3:1][O:2][C:3]([CH2:5][NH:6][CH:7]1[C:17]2[C:18]3[CH:10]([CH:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:12][C:13]=3[CH:14]=[CH:15][CH:16]=2)[CH2:9][CH2:8]1)=[O:4]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]([CH2:5][NH:6][CH:7]1[C:17]2[C:18]3[C:10](=[C:11]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[NH:12][C:13]=3[CH:14]=[CH:15][CH:16]=2)[CH2:9][CH2:8]1)=[O:4]

Participants

4

Reactant 1

HCID 19348119HCID 19348119, compound

Product 1

HCID 19348289HCID 19348289, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A portion (360 mg) of the compound obtained in Example 146 was dissolved in chloroform (60 ml) and to the solution was added active manganese dioxide (1.44 g). The mixture was heated to reflux for 2 hours. The manganese dioxide was filtered off and the filtrate was washed with a methylene chloride/methanol mixed solvent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=6:1) to yield 190 mg (53%) of the titled compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe manganese dioxide was filtered off
  4. washthe filtrate was washed with a methylene chloride/methanol mixed solvent
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-77b5066c76d34a6b8057c67070f9ea6d
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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