HCID 21612894, compound → HCID 19804929, compound

HRID 1682328Notes

Reaction equation

HRID 1682328 reaction equation
Cl.C([O:4][C:5](=[O:19])[CH:6]([NH:15][CH:16]([CH3:18])[CH3:17])/[CH:7]=[C:8](\[CH3:14])/[CH2:9][P:10]([OH:13])([OH:12])=[O:11])C>O>[CH:16]([NH:15][CH:6](/[CH:7]=[C:8](\[CH3:14])/[CH2:9][P:10]([OH:13])([OH:12])=[O:11])[C:5]([OH:19])=[O:4])([CH3:18])[CH3:17]

Participants

3

Reactant 1

HCID 21612894HCID 21612894, compound

Product 1

HCID 19804929HCID 19804929, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.20 g of E-2-isopropylamino-4-methyl-5-phosphono-3-pentenoic acid ethyl ester hydrochloride in 7 ml of water is stirred under reflux for 20 hours. The reaction mixture is concentrated to dryness by evaporation in vacuo. Ethanol is added to the residue, and the mixture is again concentrated by evaporation. This process is repeated twice more. The residue is dissolved in 25 ml of ethanol, a total of 5 ml of propylene oxide is added dropwise thereto with stirring, and the whole is concentrated to dryness by evaporation. The residue is dissolved in a little water, and ethanol is added until the solution becomes cloudy. The solution is stirred at room temperature for 4 hours to complete the reaction, during which time crystallisation slowly takes place. The product is filtered off, washed with ethanol and diethyl ether and dried at 100° under a high vacuum. In this manner there is obtained E-2-isopropylamino-4-methyl-5-phosphono-3-pentenoic acid, m.p. 225°-227° (decomp.).

Workup

  1. temperatureunder reflux for 20 hours
  2. concentrationThe reaction mixture is concentrated to dryness by evaporation in vacuo
  3. additionEthanol is added to the residue
  4. concentrationthe mixture is again concentrated by evaporation
  5. dissolutionThe residue is dissolved in 25 ml of ethanol
  6. additiona total of 5 ml of propylene oxide is added dropwise
  7. concentrationthe whole is concentrated to dryness by evaporation
  8. dissolutionThe residue is dissolved in a little water, and ethanol
  9. additionis added until the solution
  10. stirringThe solution is stirred at room temperature for 4 hours
  11. customthe reaction
  12. customduring which time crystallisation slowly takes place
  13. filtrationThe product is filtered off
  14. washwashed with ethanol and diethyl ether
  15. customdried at 100° under a high vacuum

Sources & evidence

ORD record
ord-38e54942f625440f828c00ee4bd52d22
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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