Acetic Acid → HCID 21612895, compound

HRID 728897Notes

Reaction equation

HRID 728897 reaction equation
[C:1]([O-])(=O)[CH3:2].[Na+].[CH2:6]([O:8][C:9](=[O:20])[CH:10]([NH2:19])/[CH:11]=[C:12](\[CH3:18])/[CH2:13][P:14]([OH:17])([OH:16])=[O:15])[CH3:7].[BH4-].Cl.[C:23](O)(=O)C>O.CC(C)=O>[CH2:6]([O:8][C:9](=[O:20])[CH:10]([NH:19][CH:1]([CH3:2])[CH3:23])/[CH:11]=[C:12](\[CH3:18])/[CH2:13][P:14]([OH:16])([OH:17])=[O:15])[CH3:7]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 28123BorohydrideHCID 517045Sodium AcetateHCID 63723341-Ethyl (3E)-2-amino-4-methyl-5-phosphono-3-pentenoate

Product 1

HCID 21612895HCID 21612895, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

6.64 g of sodium acetate (anhydrous) and 18 ml of acetone are added to a solution of 6.40 g of E-2-amino-4-methyl-5-phosphono-3-pentenoic acid ethyl ester in 54 ml of water and 18 ml of glacial acetic acid. 17.67 g ofsodium borohydride are added in approximately 70 portions within a period of 90 minutes with intensive cooling with ice/sodium chloride, 18 ml of acetone being added after 20 minutes and after 50 minutes. When the addition is complete, the thick white suspension is stirred at 0° for 30 minutes to complete the reaction, and then 1N hydrochloric acid is added dropwise until an acidic reaction to Congo red takes place. The resulting clear solution is concentrated by evaporation in vacuo, and the residue is concentrated by evaporation twice more after the addition of ethanol. The residue is then stirred with 200 ml of ethanol at room temperature, and the undissolved material is filtered off and washed with ethanol. The filtrate is concentrated by evaporation in vacuo, and the residue is recrystallised from isopropanol.

Workup

  1. additionadded after 20 minutes and after 50 minutes
  2. additionWhen the addition
  3. customthe reaction
  4. concentrationThe resulting clear solution is concentrated by evaporation in vacuo
  5. concentrationthe residue is concentrated by evaporation twice more
  6. additionafter the addition of ethanol
  7. stirringThe residue is then stirred with 200 ml of ethanol at room temperature
  8. filtrationthe undissolved material is filtered off
  9. washwashed with ethanol
  10. concentrationThe filtrate is concentrated by evaporation in vacuo
  11. customthe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-68ed6f8f41354a4ba952f4fe50da9275
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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