1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86743292, compound

HRID 1722632Notes

Reaction equation

HRID 1722632 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH2:13][C:14]([OH:16])=O)[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][CH:18]([P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])[P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([CH2:13][C:14]([NH:17][CH:18]([P:19](=[O:26])([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])[P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[O:16])[N:10]=[CH:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2773808Tetraethyl aminomethylenediphosphonateHCID 22161426HCID 22161426, compound

Product 1

HCID 86743292HCID 86743292, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[1-(tert-butoxycarbonyl)imidazol-4-yl]acetic acid (45 mg) and tetraethyl (aminomethylene)bis(phosphonate) (91 mg) in N,N-dimethylformamide (1 ml) was added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (42 mg) with stirring on ice-sodium chloride bath under nitrogen atmosphere. After stirring for 36 hours at 5° C., the mixture was diluted with chloroform (10 ml) and washed with cold 1N aqueous solution of citric acid (10 ml). The aqueous layer was extracted with chloroform (10 ml) twice and the combined organic layers were dried over sodium sulfate and evaporated in vacuo. The residue was dissolved in ethyl acetate (10 ml) and the solution was washed with water (10 ml), dried over sodium sulfate and evaporated in vacuo to give a colorless syrup of tetraethyl [[2-{1-(tert-butoxycarbonyl)imidazol-4-yl}acetamido]methylene]bis(phosphonate) (67 mg).

Workup

  1. stirringAfter stirring for 36 hours at 5° C.
  2. washwashed with cold 1N aqueous solution of citric acid (10 ml)
  3. extractionThe aqueous layer was extracted with chloroform (10 ml) twice
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate (10 ml)
  7. washthe solution was washed with water (10 ml)
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-6bee08c902aa40d9a0a7e50a61c8a631
Source dataset
uspto-grants-1989_08
Patent number
US04857513

Reaction notes

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