HCID 136388335, compound → HCID 178453062, compound

HRID 1861906Notes

Reaction equation

HRID 1861906 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([NH2:21])=[N:17][N+]([O-])=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)=O.CO.[Pd]>[CH:6]([OH:22])=[O:5].[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([NH2:21])=[NH:17])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 136388335HCID 136388335, compound

Product 1

HCID 178453062HCID 178453062, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent2×

Procedure

A solution of the compound (190 mg) obtained in Example 33 in 4.4% formic acid-methanol (10 ml) was added dropwise to a suspension of palladium-black (200 mg) in 4.4% formic acid-methanol (10 ml) at room temperature and stirred at room temperature for 16 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure; the resulting residue was purified by silica gel column chromatography (eluent, chloroform methanol=8:2) to give 71 mg of the titled compound (yield, 37%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluent, chloroform methanol=8:2)

Sources & evidence

ORD record
ord-c3a8028a1a914944901506cc76f7061f
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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