Triethylamine → Diethyl 2-carbamimidoylpentane-1,5-dioate

HRID 570703Notes

Reaction equation

HRID 570703 reaction equation
Cl.[NH2:2][C:3](=[NH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20].C(=O)([O-])O.[Na+]>C(O)C>[C:3]([CH:4]([CH2:20][CH2:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[NH:2])[NH2:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 516892Sodium BicarbonateHCID 15555354Ethyl 2-carbamimidoylacetate hydrochloride

Product 1

HCID 86685366Diethyl 2-carbamimidoylpentane-1,5-dioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-amino-3-iminopropionoate hydrochloride (10 g) and triethylamine (18.4 mL) in ethanol (100 mL) was added ethyl acrylate (7.15 mL), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.5 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-add93d70cfe74ff1989783ef734130cd
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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