Hydrochloric Acid → 1-Ethyl (3E)-2-amino-4-methyl-5-phosphono-3-pentenoate

HRID 728851Notes

Reaction equation

HRID 728851 reaction equation
[NH2:1][CH:2](/[CH:6]=[C:7](\[CH3:13])/[CH2:8][P:9]([OH:12])([OH:11])=[O:10])[C:3]([OH:5])=[O:4].Cl.[CH2:15](O)[CH3:16]>>[CH2:15]([O:4][C:3](=[O:5])[CH:2]([NH2:1])/[CH:6]=[C:7](\[CH3:13])/[CH2:8][P:9]([OH:12])([OH:11])=[O:10])[CH3:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5950212CGP 37849

Product 1

HCID 63723341-Ethyl (3E)-2-amino-4-methyl-5-phosphono-3-pentenoate

Procedure

2.0 g of E-2-amino-4-methyl-5-phosphono-3-pentenoic acid are placed in 50 ml of ethanol and the whole is saturated with hydrogen chloride gas for21/2 hours at 50°. After concentration, the residue is dissolved in 20 ml of ethanol, 20 ml of propylene oxide are added and the precipitate is filtered off. Recrystallisation from water/ethanol (1:3) yields E-2-amino-4-methyl-5-phosphono-3-pentenoic acid ethyl ester, m.p. 193°-194°.

Workup

  1. custom2 hours
  2. customat 50°
  3. concentrationAfter concentration
  4. dissolutionthe residue is dissolved in 20 ml of ethanol
  5. addition20 ml of propylene oxide are added
  6. filtrationthe precipitate is filtered off
  7. customRecrystallisation from water/ethanol (1:3)

Sources & evidence

ORD record
ord-c400966d74d44fa49814ec113d76b886
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

Loading…