HCID 86757331, compound → HCID 86757330, compound

HRID 651822Notes

Reaction equation

HRID 651822 reaction equation
C([O:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:23]([NH:25][N:26]1[C:30](=[O:31])[C:29](=[O:32])[N:28]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:27]1=[O:40])=[O:24])[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11])C1C=CC=CC=1>CO.[Pd]>[CH2:33]([N:28]1[C:29](=[O:32])[C:30](=[O:31])[N:26]([NH:25][C:23](=[O:24])[C@@H:22]([C@@H:12]([C:10](=[O:11])[NH:9][OH:8])[CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:41][CH:42]([CH3:43])[CH3:44])[C:27]1=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 1

HCID 86757331HCID 86757331, compound

Product 1

HCID 86757330HCID 86757330, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.076 g of (E)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-N-(3-benzyl-2,4,5-trioxo-1-imidazolidinyl]-4-methylvaleramide in 5 ml of methanol was hydrogenated in the presence of 0.025 g of 5% palladium-on-carbon for 6 hours. The catalyst was removed by filtration and the mixture evaporated. The residue was redissolved in 5 ml of methanol and hydrogenated in the presence of 0.020 g of 10% palladium-on-carbon for 3 hours. The catalyst was removed by filtration and the solvent was evaporated and the residue was then triturated with hexane and then with diethyl ether to give 0.022 g of N-(3-benzyl-2,4,5-trioxo-1-imidazolidinyl]-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methylvaleramide in the form of a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe mixture evaporated
  3. dissolutionThe residue was redissolved in 5 ml of methanol and hydrogenated in the presence of 0.020 g of 10% palladium-on-carbon for 3 hours
  4. customThe catalyst was removed by filtration
  5. customthe solvent was evaporated
  6. customthe residue was then triturated with hexane

Sources & evidence

ORD record
ord-755afb5abe39497999f1cee1e6905b60
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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