Water → Di-tert-butyl 7-amino-6,8-dioxo-2,5,9,12-tetraazatridecanedioate

HRID 459654

Reaction equation

HRID 459654 reaction equation
[NH2:1][CH:2]([C:8]([O:10]CC)=O)[C:3]([O:5]CC)=O.[NH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].[OH2:24]>C(Cl)(Cl)Cl>[NH2:1][CH:2]([C:3](=[O:5])[NH:13][CH2:14][CH2:15][NH:16][C:17]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:24])[C:8](=[O:10])[NH:13][CH2:14][CH2:15][NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 81272Propanedioic acid, 2-amino-, 1,3-diethyl esterHCID 187201N-BOC-ethylenediamine2×

Product 1

HCID 18442407Di-tert-butyl 7-amino-6,8-dioxo-2,5,9,12-tetraazatridecanedioate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of diethyl 2-aminomalonate (1.68 g) and tert-butyl (2-aminoethyl)carbamate (3.20 g) in dehydrated chloroform (5 ml) was stirred under reflux. After 7 hours, additional tert-butyl (2-aminoethyl)carbamate (3.20 g) was added to the reaction mixture, and the mixture was stirred under reflux for 2 days. To the reaction mixture was added water, and the solution was washed with a mixed solvent of hexane and diisopropyl ether (1:1). The aqueous layer was extracted with methylene chloride. The organic layer was washed with water and extracted with 5% aqueous citric acid solution. The aqueous layer was washed with diethyl ether and basified with sodium hydroxide. The aqueous solution was extracted with methylene chloride. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with a mixed solvent of diisopropyl ether and diethyl ether to give di-tert-butyl 7-amino-6,8-dioxo-2,5,9,12-tetraazatridecanedioate (1.87 g) as a solid.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux for 2 days
  3. washthe solution was washed with a mixed solvent of hexane and diisopropyl ether (1:1)
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. washThe organic layer was washed with water
  6. extractionextracted with 5% aqueous citric acid solution
  7. washThe aqueous layer was washed with diethyl ether and basified with sodium hydroxide
  8. extractionThe aqueous solution was extracted with methylene chloride
  9. washThe organic layer was washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was triturated with a mixed solvent of diisopropyl ether and diethyl ether

Sources & evidence

ORD record
ord-087d35306bc54ab79cf4facf31ca8757
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Linked notes

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