(2-Aminoethyl)phosphonic acid → Maleimidoethane Phosphonic Acid

HRID 1452002Notes

Reaction equation

HRID 1452002 reaction equation
C(OC([C:6]1[C:7]([NH:9][C:10](=[O:12])[CH:11]=1)=[O:8])=O)C.N[CH2:14][CH2:15][P:16](=[O:19])([OH:18])[OH:17].C(=O)([O-])[O-].[Na+].[Na+].S(=O)(=O)(O)O>O>[C:10]1(=[O:12])[N:9]([CH:15]([P:16]([OH:19])(=[O:17])[OH:18])[CH3:14])[C:7](=[O:8])[CH:6]=[CH:11]1

Participants

6

Reactant 4

HCID 339(2-Aminoethyl)phosphonic acidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 22915910Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carboxylate

Product 1

HCID 67705894Maleimidoethane Phosphonic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Ethoxy carbonyl maleimide, 169 mg, was added to 2-aminoethyl phosphonic acid, 125 mg, and sodium carbonate, 106 mg, in 1 ml of water at 0° C. The mixture was stirred for 20 minutes, then 4 ml of water was added and the mixture was stirred at room temperature for 1 hr. The solution was acidified to pH 5.5 with dilute sulfuric acid and concentrated in vacuo to 1 ml. The product was isolated by chromatography on three 1000μ reverse-phase TLC plates developed in water. Four bands were noted on examination of the developed plates under U.V. light. The third band at 15-16.7 cm from the origin was isolated; 100 mg of maleimidoethane phosphonic acid-sodium salt was recovered as an amorphous powder. The 200 MHZ NMR spectrum in D2O showed the maleimide hydrogens as a singlet at 7,2 ppm and the ethylene hydrogens as multiplets at 4.0 and 2.2 ppm.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. concentrationconcentrated in vacuo to 1 ml
  3. customThe product was isolated by chromatography on three 1000μ reverse-phase TLC plates
  4. customThe third band at 15-16.7 cm from the origin was isolated
  5. custom100 mg of maleimidoethane phosphonic acid-sodium salt was recovered as an amorphous powder

Sources & evidence

ORD record
ord-473b4df71a4e4669a262cf2ab0aba8f6
Source dataset
uspto-grants-1997_02
Patent number
US05606030

Reaction notes

Loading…