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

HRID 557473

Reaction equation

HRID 557473 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-1079f7c1cd5d4a2db7acc72a56001f20
Source dataset
uspto-grants-2011_11
Patent number
US08058456B2

Linked notes

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