ethyl 3-[N,N'-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylate → Ethyl 3-amino-2,5-dioxopyrrolidine-3-carboxylate

HRID 1943005Notes

Reaction equation

HRID 1943005 reaction equation
C(OC([N:11]([C:23]1([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29])NC(OCC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pt]=O>[NH2:11][C:23]1([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29]

Participants

5

Reactant 2

HCID 58382718ethyl 3-[N,N'-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19785423Ethyl 3-amino-2,5-dioxopyrrolidine-3-carboxylateYield 64.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound of Example 1 (496 mg) in acetic acid (15 ml) was added platinum oxide (102 mg). This mixture was stirred vigorously at 50° C. under hydrogen (atmospheric pressure) for 6 hours. During this reaction, to remove carbon dioxide generated with the progress of the reaction, the gas in the reactor was replaced with hydrogen gas several times. The reaction mixture was filtered through a Celite pad and then the Celite was washed with a small amount of acetic acid. The filtrate combined with the washers was concentrated and to the resulting residue was added toluene to remove azeotropically the residual acetic acid and then the mixture was concentrated again. To the residue was added ethyl acetate and the insoluble material was filtered off, and then the ethyl acetate solution was concentrated to give a crude product which was then purified by a flash column chromatography (chloroform:methanol=30:1) to give the desired product (126 mg, 64%) as crystal. 1H NMR (CDCl3) data of this product were consistent with those of an optical active substance described in J. Med. Chem., 1998, 41, p. 4118 to 4129.

Workup

  1. customDuring this reaction
  2. customto remove carbon dioxide
  3. customgenerated with the progress of the reaction
  4. filtrationThe reaction mixture was filtered through a Celite pad
  5. washthe Celite was washed with a small amount of acetic acid
  6. concentrationwas concentrated and to the resulting residue
  7. additionwas added toluene
  8. customto remove azeotropically the residual acetic acid
  9. concentrationthe mixture was concentrated again
  10. additionTo the residue was added ethyl acetate
  11. filtrationthe insoluble material was filtered off
  12. concentrationthe ethyl acetate solution was concentrated
  13. customto give a crude product which
  14. customwas then purified by a flash column chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-4e0e1e5da9104ddab5fad148cd440075
Source dataset
uspto-grants-2013_03
Patent number
US08389742B2

Reaction notes

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