HCID 86757325, compound → HCID 86757324, compound

HRID 651816Notes

Reaction equation

HRID 651816 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11](=[O:13])[N:10]([NH:14][C:15](=[O:42])[C@@H:16]([C@@H:21]([C:31](=[O:41])[NH:32][O:33]CC2C=CC=CC=2)[CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])[C:9]1=[O:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([N:8]1[CH2:12][C:11](=[O:13])[N:10]([NH:14][C:15](=[O:42])[C@@H:16]([C@@H:21]([C:31](=[O:41])[NH:32][OH:33])[CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:17][CH:18]([CH3:19])[CH3:20])[C:9]1=[O:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86757325HCID 86757325, compound

Product 1

HCID 86757324HCID 86757324, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.1 g of N-(3-benzyl-2,5-dioxo-1-imidazolidinyl)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-4-methylvaleramide in 20 ml of methanol was hydrogenated in the presence of 0.100 g of 10% palladium-on-carbon for 3 hours. The mixture was filtered and evaporated and the residue was triturated with diethyl ether to give 0.444 g of N-(3-benzyl-2,5-dioxo-1-imidazolidinyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methylvaleramide in the form of a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-07a875f8dd734a34ba538a0ba82a375e
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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