HCID 178525808, compound → HCID 178525809, compound

HRID 1655734Notes

Reaction equation

HRID 1655734 reaction equation
C([O:8][C:9](=[O:35])[C@@H:10]([O:17][C:18](=[O:34])[CH:19]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:27]([CH:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:18]([O:17][C@@H:10]([CH2:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)[C:9]([OH:35])=[O:8])=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 178525808HCID 178525808, compound

Product 1

HCID 178525809HCID 178525809, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.2 g (6.83 mmol) of (S)-α-(dibenzylacetoxy)imidazole-4-propionic acid benzyl ester in 150 ml of methanol were hydrogenated at room temperature for 2 hours in the presence of 660 mg of palladium-on-carbon. The catalyst was filtered off and the filter residue was washed several times with a 1:1 mixture of methylene chloride and methanol. The solution was concentrated under reduced pressure until crystallization occurred. Recrystallization of the crystallizate from methylene chloride/methanol yielded 2.5 g (96%) of (S)-α-(dibenzylacetoxy)imidazole-4-propionic acid, melting point 210°.

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe filter residue was washed several times
  3. additionwith a 1:1 mixture of methylene chloride and methanol
  4. concentrationThe solution was concentrated under reduced pressure until crystallization
  5. customRecrystallization of the crystallizate from methylene chloride/methanol

Sources & evidence

ORD record
ord-f712c1e260a840198b54a43a5a95df01
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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