1,2-dibenzyl 1-tert.butyl 4-methyl-1-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl)methyl]-1,1,2(R)-pentanetricarboxylate → 1-(tert.butoxycarbonyl)-4-methyl-1-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl) methyl]-1,2(R)-pentanedicarboxyic acid

HRID 2399229Notes

Reaction equation

HRID 2399229 reaction equation
[CH3:1][CH:2]([CH3:43])[CH2:3][C@@H:4]([C:33]([O:35]CC1C=CC=CC=1)=[O:34])[C:5]([CH2:23][N:24]1[C:28](=[O:29])[N:27]([CH3:30])[N:26]([CH3:31])[C:25]1=[O:32])([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:6]([O:8]CC1C=CC=CC=1)=[O:7]>CO.[Pd]>[C:19]([O:18][C:16]([C:5]([CH2:23][N:24]1[C:25](=[O:32])[N:26]([CH3:31])[N:27]([CH3:30])[C:28]1=[O:29])([C:6]([OH:8])=[O:7])[C@H:4]([C:33]([OH:35])=[O:34])[CH2:3][CH:2]([CH3:43])[CH3:1])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 1

HCID 700435121,2-dibenzyl 1-tert.butyl 4-methyl-1-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl)methyl]-1,1,2(R)-pentanetricarboxylate

Product 1

HCID 700533491-(tert.butoxycarbonyl)-4-methyl-1-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl) methyl]-1,2(R)-pentanedicarboxyic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.464 g of 1,2-dibenzyl 1 -tert.butyl 4-methyl-1 -[(1,2-dimethyl-3,5-dioxo- 1,2,4-triazolidin-4-yl)methyl]-1,1,2(R)-pentanetricarboxylate were dissolved in 40 ml of methanol containing 0.25 g of 10% palladium-on-charcoal catalyst. The mixture was hydrogenated for 2 hours, the catalyst was removed by filtration and the solvent evaporated to give 1-(tert.butoxycarbonyl)-4-methyl-1-[(1,2-dimethyl-3,5-dioxo-1,2,4-triazolidin-4-yl) methyl]-1,2(R)-pentanedicarboxyic acid in the form of a colorless gum. The gum was dissolved in 60 ml of toluene containing 0.43 ml of N-methylmorpholine and the mixture was heated under reflux for 1 hour. The solution was washed with 5% aqueous citric acid solution, water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated to give 1.422 g of 2(R)-[1(R or S)-(tert.butoxycarbonyl)-2-(1,2-dimethyl-3,5-clioxo-1,2,4-triazolidin-4-yl) ethyl]-4-methylvaleric acid in the form of a waxy solid as an approximately 6:1 mixture of diastereoisomer 1 and diastereoisomer 2.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-8ba7f3d6a191452d93f88fd587bf8759
Source dataset
uspto-grants-1995_09
Patent number
US05447929

Reaction notes

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