HCID 22908979, compound → HCID 22909002, compound

HRID 1378992Notes

Reaction equation

HRID 1378992 reaction equation
[OH:1][CH2:2][C:3]1[N:11]([CH3:12])[C:10]2[C:9](=[O:13])[N:8]([CH2:14][CH2:15][CH3:16])[C:7](=[O:17])[N:6]([CH2:18][CH2:19][CH3:20])[C:5]=2[N:4]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:12][N:11]1[C:10]2[C:9](=[O:13])[N:8]([CH2:14][CH2:15][CH3:16])[C:7](=[O:17])[N:6]([CH2:18][CH2:19][CH3:20])[C:5]=2[N:4]=[C:3]1[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 22908979HCID 22908979, compound

Product 1

HCID 22909002HCID 22909002, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese dioxide (2.48 g, 28.5 mmol) was added to a solution of 800 mg (2.85 mmol) of Compound b obtained in Reference Example 2 in 80 ml of chloroform, and the mixture was stirred at room temperature for 12 hours. Then, the reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluent: 1% methanol/chloroform) to give 440 mg (yield 56%) of Compound c as a pale yellow powder.

Workup

  1. filtrationThen, the reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (eluent: 1% methanol/chloroform)

Sources & evidence

ORD record
ord-885feaab218a49feb723b155f4899c18
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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