HCID 86745092, compound → HCID 67919276, compound

HRID 1682305Notes

Reaction equation

HRID 1682305 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([NH:24]C=O)/[CH:6]=[C:7](\[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)/[CH2:8][P:9]([O:14]CC)([O:11]CC)=[O:10])C>Cl>[NH2:24][CH:5](/[CH:6]=[C:7](\[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)/[CH2:8][P:9]([OH:14])([OH:11])=[O:10])[C:4]([OH:27])=[O:3]

Participants

3

Reactant 1

HCID 86745092HCID 86745092, compound

Product 1

HCID 67919276HCID 67919276, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

0.44 g of E-2-formylamino-4-benzyl-5-diethylphosphono-3-pentenoic acid ethyl ester are dissolved in ml of 4.5 N hydrochloric acid and heated at 85° for hours. After concentration in vacuo, the residue is dissolved in a small amount of ethanol and 1 ml of ethanol/propylene oxide (1:1) is added dropwise thereto. The resulting white precipitate is filtered off and, after recrystallisation from water, E-2-amino-4-benzyl-5-phosphono-3-pentenoic acid is obtained in the form of colourless needles, m.p. 196°-198°.

Workup

  1. temperatureheated at 85° for hours
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe residue is dissolved in a small amount of ethanol and 1 ml of ethanol/propylene oxide (1:1)
  4. additionis added dropwise
  5. filtrationThe resulting white precipitate is filtered off
  6. customafter recrystallisation from water

Sources & evidence

ORD record
ord-50d253f92bd740d4b2c71e51c4969375
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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