3-Allyloxy-N-[(1S,2S,4R)-1-benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-5-(2-oxopyrrolidin-1-yl)-benzamide → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-propoxybenzamide

HRID 1612477Notes

Reaction equation

HRID 1612477 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:33]=[C:34]([N:36]2[CH2:40][CH2:39][CH2:38][C:37]2=[O:41])[CH:35]=1)[C:8]([NH:10][C@@H:11]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@@H:12]([OH:25])[CH2:13][C@H:14]([C:16](=[O:24])[NH:17][CH2:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:15])=[O:9])[CH:2]=[CH2:3]>CO.S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O>[CH2:26]([C@H:11]([NH:10][C:8](=[O:9])[C:7]1[CH:6]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:35]=[C:34]([N:36]2[CH2:40][CH2:39][CH2:38][C:37]2=[O:41])[CH:33]=1)[C@@H:12]([OH:25])[CH2:13][C@H:14]([C:16](=[O:24])[NH:17][CH2:18][CH2:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH3:15])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 101965983-Allyloxy-N-[(1S,2S,4R)-1-benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-5-(2-oxopyrrolidin-1-yl)-benzamide

Product 1

HCID 10175116N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-propoxybenzamide

Reagents, catalysts & solvents 2

HCID 17887766Palladium barium sulphateCatalystHCID 887MethanolSolvent

Procedure

The allyl compound of E3 (0.042 g) was hydrogenated in methanol (5 ml) in the presence of 5% palladium-barium sulfate (0.020 g) for 3 hrs. The mixture was filtered through celite and evaporated to give the title compound.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-659d2d66b187454faa605bea58a570e5
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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