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

HRID 1675929Notes

Reaction equation

HRID 1675929 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][C:4](=[O:12])[NH:3]1.[N:13]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[N:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH2:28]([O:27][C:25]([N:13]([C:6]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][C:4](=[O:12])[NH:3][C:2]1=[O:1])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 23635561Ethyl 2,5-dioxo-3-pyrrolidinecarboxylate

Product 1

HCID 58382718ethyl 3-[N,N'-bis(benzyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2,5-dioxopyrrolidine-3-carboxylate (3.92 g) in ethyl acetate (60 ml) was added dibenzyl azodicarboxylate (7.27 g), followed by potassium carbonate (317 mg) at room temperature. After this mixture was stirred at room temperature for 1 hour, the mixture was filtered through a Celite pad. The filtrate was concentrated and the resulting residue was purified by a flash column chromatography (hexane:ethyl acetate=2:1) to give the desired product (10.1 g, 94%) as amorphous.

Workup

  1. filtrationthe mixture was filtered through a Celite pad
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified by a flash column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2099781888e647749a6a72c2fc8f938c
Source dataset
uspto-grants-2011_08
Patent number
US08003808B2

Reaction notes

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