2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide → 2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide

HRID 651801Notes

Reaction equation

HRID 651801 reaction equation
C([O:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:23]([NH:25][N:26]1[C:30](=[O:31])[CH2:29][NH:28][C:27]1=[O:32])=[O:24])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11])C1C=CC=CC=1>CO.[Pd]>[OH:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:23]([NH:25][N:26]1[C:30](=[O:31])[CH2:29][NH:28][C:27]1=[O:32])=[O:24])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:11]

Participants

4

Reactant 1

HCID 867573102(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide

Product 1

HCID 867573092(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramideYield 17.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.290 g of 2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide in 10 ml of methanol was hydrogenated for 2 hours in the presence of 0.087 g of 5% palladium-on-carbon. The catalyst was removed by filtration and evaporation of the solvent gave a residue which was purified by flash column chromatography on silica gel using dichloromethane/methanol (95:5) for the elution to give 0.042 g of 2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,5-dioxo-1-imidazolidinyl)valeramide in the form of a white solid.

Workup

  1. customThe catalyst was removed by filtration and evaporation of the solvent
  2. customgave a residue which
  3. customwas purified by flash column chromatography on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-1bd49f54d7ba4f979aea2a1b79edfaf7
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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