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

HRID 728879Notes

Reaction equation

HRID 728879 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH:16]C=O)/[CH:6]=[C:7](\[CH3:15])/[CH2:8][P:9]([O:13]C)([O:11]C)=[O:10])[CH3:2].C[Si](C)(C)Br.C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH2:16])/[CH:6]=[C:7](\[CH3:15])/[CH2:8][P:9]([OH:11])([OH:13])=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 21612902HCID 21612902, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

16.9 g of E-2-formylamino-4-methyl-5-dimethylphosphono-3-pentenoic acid ethyl ester are dissolved in 80 ml of dichloromethane under a nitrogen atmosphere, and 30 ml of trimethylbromosilane are added dropwise at approximately 25° within a period of 30 minutes. The mixture is stirred at room temperature for 20 hours, and then 80 ml of ethanol are added dropwise at approximately 25° within a period of 30 minutes. The mixture is then again stirred at room temperature for 22 hours and is then concentrated by evaporation. The residue is dissolved in 80 ml of ethanol, and 80 ml of propylene oxide in 80 ml of ethanol are added dropwise with slight cooling. The mixture is stirred at room temperature for one hour to complete the reaction, filtered and washed with ethanol and ether. In this manner there is obtained E-2-amino-4-methyl-5-phosphono-3-pentenoic acid ethyl ester, m.p. 215°-217° (decomp.).

Workup

  1. stirringThe mixture is then again stirred at room temperature for 22 hours
  2. concentrationis then concentrated by evaporation
  3. dissolutionThe residue is dissolved in 80 ml of ethanol
  4. addition80 ml of propylene oxide in 80 ml of ethanol are added dropwise with slight cooling
  5. stirringThe mixture is stirred at room temperature for one hour
  6. customthe reaction
  7. filtrationfiltered
  8. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-2390e1f7c9db4f64bac82d9127794d19
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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