HCID 86757319, compound → HCID 86757318, compound

HRID 651810Notes

Reaction equation

HRID 651810 reaction equation
C([O:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:23]([NH:25][N:26]1[C:30](=[O:31])[N:29]([CH3:32])[NH:28][C:27]1=[O:33])=[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]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:23]([NH:25][N:26]1[C:30](=[O:31])[N:29]([CH3:32])[NH:28][C:27]1=[O:33])=[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 86757319HCID 86757319, compound

Product 1

HCID 86757318HCID 86757318, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.229 g of 2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(1-methyl-3,5-dioxo-1,2,4-triazolidin-4-yl)valeramide in 20 ml of methanol was hydrogenated in the presence of 0.02 g of 10% palladium-on-carbon for 5 hours. Filtration and evaporation gave a residue which was triturated with diethyl ether to give 0.135 g of 2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(1-methyl-3,5-dioxo-1,2,4-triazolidin-4-yl)valeramide in the form of a white solid.

Workup

  1. filtrationFiltration and evaporation
  2. customgave a residue which
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-83b756ac08704b88912ddec309e1fef5
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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