HCID 21667321, compound → HCID 67918842, compound

HRID 1682308Notes

Reaction equation

HRID 1682308 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([NH:22]C=O)/[CH:5]=[C:6](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)/[CH2:7][P:8]([O:13]CC)([O:10]CC)=[O:9]>Cl>[NH2:22][CH:4](/[CH:5]=[C:6](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)/[CH2:7][P:8]([OH:13])([OH:10])=[O:9])[C:3]([OH:25])=[O:2]

Participants

3

Reactant 1

HCID 21667321HCID 21667321, compound

Product 1

HCID 67918842HCID 67918842, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

0.15 g of E-2-formylamino-4-phenyl-5-diethylphosphono-3-pentenoic acid methyl ester are dissolved in 10 ml of 4.5 N hydrochloric acid and heated at 75° for 192 hours. After concentration in vacuo, the foamy 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 recrystallised from water/acetone (1:2). E-2-amino-4-phenyl-5-phosphono-3-pentenoic acid is thus obtained in the form of colourless needles, m.p. 230°-233°.

Workup

  1. temperatureheated at 75° for 192 hours
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe foamy 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. customrecrystallised from water/acetone (1:2)

Sources & evidence

ORD record
ord-46286d00b3ad4c5ea8fd01ae6bfb5362
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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