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

HRID 1964177Notes

Reaction equation

HRID 1964177 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:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[C:25]([O:24][C:22]([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][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97268Di-tert-butyl azodicarboxylateHCID 23635561Ethyl 2,5-dioxo-3-pyrrolidinecarboxylate

Product 1

HCID 67342586ethyl 3-[N,N'-bis(tert-butyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylateYield 83.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2,5-dioxopyrrolidine-3-carboxylate (2.96 g) in ethyl acetate (25 ml) were added di-tert-butyl azodicarboxylate (4.19 g) and then potassium carbonate (4.78 g) at room temperature. After this reaction mixture was stirred at room temperature for 15 minutes, the resulting mixture was filtered through a Celite pad and the filtrate was concentrated. The residue was purified by a flash column chromatography (hexane:ethyl acetate=3:1) to give ethyl 3-[N,N′-bis(tert-butyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxy late (5.77 g, 83%) as amorphous.

Workup

  1. customat room temperature
  2. filtrationthe resulting mixture was filtered through a Celite pad
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by a flash column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-85bf5424c8bf487f8e30f26cb40953fc
Source dataset
uspto-grants-2013_04
Patent number
US08415487B2

Reaction notes

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