HCID 86589022, compound → HCID 23513980, compound

HRID 353477Notes

Reaction equation

HRID 353477 reaction equation
[O:1]=[C:2]([NH:32][C:33]1[CH2:34][O:35][C:36](=[O:38])[CH:37]=1)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24]CC3C=CC=CC=3)=[O:23])=[CH:17][CH:16]=2)[CH:6]=1)=[O:4]>CN(C=O)C.[Pd].O.C(O)C>[O:1]=[C:2]([NH:32][C:33]1[CH2:34][O:35][C:36](=[O:38])[CH:37]=1)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:19][CH:20]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 1

HCID 86589022HCID 86589022, compound

Product 1

HCID 23513980HCID 23513980, compoundYield 64.8%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of benzyl {4-[(3-{oxo[(5-oxo-2,5-dihydro-3-furanyl)amino]acetyl}-1H-indol-1-yl)methyl]phenyl}acetate (300 mg) in DMF (10 ml) is hydrogenated at room temperature and pressure in the presence of 10% palladium on charcoal (60 mg of a 50% wt/wt suspension in water). After 3 h30′ the catalyst is removed by filtration and the filtrate is concentrated to dryness. The residue obtained is suspended in absolute ethanol and recovered by filtration, to give {4-[(3-{oxo[(5-oxo-2,5-dihydro-3-furanyl)amino]acetyl}-1H-indol-1-yl)methyl]phenyl}acetic acid (160 mg).

Workup

  1. customis hydrogenated at room temperature
  2. customAfter 3 h30′ the catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe residue obtained
  5. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-603569efd3d14936a5a73df54bcb2ce3
Source dataset
uspto-grants-2004_06
Patent number
US06753342B2

Reaction notes

Loading…