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

HRID 1943007Notes

Reaction equation

HRID 1943007 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) was added di-tert-butyl azodicarboxylate (4.19 g), followed by 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 the desired product (5.77 g, 83%) as amorphous.

Workup

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

Sources & evidence

ORD record
ord-6d45466d341b447c8ab746b1e738c0b8
Source dataset
uspto-grants-2013_03
Patent number
US08389742B2

Reaction notes

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