HCID 21667319, compound → HCID 6506250, compound

HRID 1682268Notes

Reaction equation

HRID 1682268 reaction equation
C([O:3][C:4](=[O:20])[CH:5]([NH:17]C=O)/[CH:6]=[CH:7]/[CH2:8][P:9]([O:14]CC)([O:11]CC)=[O:10])C>Cl>[NH2:17][CH:5](/[CH:6]=[CH:7]/[CH2:8][P:9]([OH:14])([OH:11])=[O:10])[C:4]([OH:20])=[O:3]

Participants

3

Reactant 1

HCID 21667319HCID 21667319, compound

Product 1

HCID 6506250HCID 6506250, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

8.22 g of E-2-formylamino-5-diethylphosphono-3-pentenoic acid ethyl ester are dissolved in 170 ml of 6 N hydrochloric acid and the whole is heated under reflux for 22 hours. After concentration in vacuo, the oily residue is taken up in a small amount of ethanol and the mixture is again concentrated by evaporation in vacuo. This procedure is repeated a further twice. The resulting residue is dissolved in 15 ml of ethanol and 20 ml of ethanol/propylene oxide (1:1) are added dropwise. The resulting brownish-coloured precipitate is filtered off and purified by ion exchange chromatography (Dowex 500W×8/H2O). After concentration and lyophilisation, E-2-amino-5-phosphono-3-pentenoic acid is obtained in the form of a white amorphous powder, 1H-NMR (D2O): 2.39 (dd, 2H, C(5)-H); 4.27 (d, 1H, C(2)-H); 5.53 (m, 1H, C(3)-H); 5.87 (m, 1H, C(4)-H), m.p. after recrystallisation from ethanol/water 191°-192° .

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux for 22 hours
  3. concentrationAfter concentration in vacuo
  4. concentrationthe mixture is again concentrated by evaporation in vacuo
  5. dissolutionThe resulting residue is dissolved in 15 ml of ethanol
  6. addition20 ml of ethanol/propylene oxide (1:1) are added dropwise
  7. filtrationThe resulting brownish-coloured precipitate is filtered off
  8. custompurified by ion exchange chromatography (Dowex 500W×8/H2O)
  9. concentrationAfter concentration and lyophilisation

Sources & evidence

ORD record
ord-f3441c632fd24d6ea71fece658d010c1
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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