(4R)-3-[(Benzyloxy)carbonyl]-2-oxoimidazolidine-4-carboxylic acid → (4R)-2-oxoimidazolidine-4-carboxylic acid

HRID 83549Notes

Reaction equation

HRID 83549 reaction equation
C(OC([N:11]1[C@@H:15]([C:16]([OH:18])=[O:17])[CH2:14][NH:13][C:12]1=[O:19])=O)C1C=CC=CC=1.[H][H]>CO.O1CCCC1.[Pd]>[O:19]=[C:12]1[NH:11][C@@H:15]([C:16]([OH:18])=[O:17])[CH2:14][NH:13]1

Participants

5

Reactant 2

HCID 688195(4R)-3-[(Benzyloxy)carbonyl]-2-oxoimidazolidine-4-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 7003745(4R)-2-oxoimidazolidine-4-carboxylic acidYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a solution of (R)-2-oxoimidazolidine-1,5-dicarboxylic acid 1-benzyl ester (1.61 g) in methanol/tetrahydrofuran (4/1, 20 ml) was added 10 wt % palladium on carbon (161 mg) at room temperature, and the mixture was stirred for 24 hours under one atmosphere of hydrogen. Under nitrogen atmosphere, palladium on carbon in this reaction solution was filtered off through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue were added diisopropyl ether and n-hexane, and the mixture was stirred. A solid was collected from this suspension by filtration, and dried under reduced pressure to give the titled compound (565 mg).

Workup

  1. filtrationUnder nitrogen atmosphere, palladium on carbon in this reaction solution was filtered off through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the resulting residue were added diisopropyl ether and n-hexane
  4. filtrationA solid was collected from this suspension by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1a00e101946843eba1f536e4a40960ca
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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