HCID 74983000, compound → HCID 74983000, compound

HRID 1913577Notes

Reaction equation

HRID 1913577 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH:32]=[CH:31][C:14]([O:15][C:16]([C:18]2[O:22][C:21]([CH2:23][CH:24]([CH3:30])[CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:20][CH:19]=2)=[O:17])=[CH:13][CH:12]=1)(=[NH:10])[NH2:9]>C(O)C.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH:32]=[CH:31][C:14]([O:15][C:16]([C:18]2[O:22][C:21]([CH2:23][CH:24]([CH3:30])[CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:20][CH:19]=2)=[O:17])=[CH:13][CH:12]=1)(=[NH:9])[NH2:10]

Participants

5

Reactant 1

HCID 74983000HCID 74983000, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 74983000HCID 74983000, compoundYield 137.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the compound (149 mg, 0.435 mmol) obtained in step 2 in ethanol (3 mL) was added 5% palladium/carbon (15 mg), and the mixture was stirred under a hydrogen atmosphere for 9 hours. The catalyst was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by high performance liquid chromatography (water-acetonitrile, each containing 0.1% trifluoroacetic acid) to give the title compound (75 mg, 0.30 mmol, 68%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by high performance liquid chromatography (water-acetonitrile

Sources & evidence

ORD record
ord-8bdc541defa64e9ea435e3d730e07037
Source dataset
uspto-grants-2013_12
Patent number
US08609715B2

Reaction notes

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