HCID 59902684, compound → HCID 59902669, compound

HRID 2230420Notes

Reaction equation

HRID 2230420 reaction equation
C([O:4][C@@H:5]([C@H:23]([O:54]C(=O)C)[C@H:24]([O:50]C(=O)C)[C@@H:25]([NH:31][C:32](=[O:49])[C@H:33]([CH2:45][CH:46]([CH3:48])[CH3:47])[NH:34]C(OCC1C=CC=CC=1)=O)[CH2:26][O:27]C(=O)C)[C:6]([NH:8][C@H:9]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[CH2:10][C:11]([O:13]CC)=[O:12])=[O:7])(=O)C>CO.[Pd]>[OH:4][C@@H:5]([C@H:23]([OH:54])[C@H:24]([OH:50])[C@@H:25]([NH:31][C:32](=[O:49])[C@H:33]([CH2:45][CH:46]([CH3:48])[CH3:47])[NH2:34])[CH2:26][OH:27])[C:6]([NH:8][C@H:9]([C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=1)[CH2:10][C:11]([OH:13])=[O:12])=[O:7]

Participants

4

Reactant 1

HCID 59902684HCID 59902684, compound

Product 1

HCID 59902669HCID 59902669, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl (S)-3-[(2S,3R,4 R,5S)-2,3,4,6-tetraacetoxy-5-(N-benzyloxycarbonyl-L-leucyl)aminohexanoyl]amino-3-(4-methylphenyl)propionate (184 mg) in methanol (10 ml) was stirred at room temperature with 10% palladium on activated carbon (100 mg) under hydrogen atmosphere for 2 hours. After filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (10 ml) and to the solution was added 1N aqueous sodium hydroxide solution (2.2 ml) under ice-cooling. The mixture was stirred under ice-cooling for 1hour, followed by addition of 1N hydrochloric acid (2.2 ml). After concentration under reduced pressure, the residue was passed through a column of DIAION HP-20SS (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to afford the title compound (50 mg).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (10 ml) and to the solution
  4. additionwas added 1N aqueous sodium hydroxide solution (2.2 ml) under ice-
  5. temperaturecooling
  6. temperaturecooling for 1hour
  7. additionfollowed by addition of 1N hydrochloric acid (2.2 ml)
  8. concentrationAfter concentration under reduced pressure
  9. washfollowed by elution with water-acetonitrile
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-fbd5c9ae0cfa4fc69c32d3b14cb7300d
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

Loading…