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

HRID 1682314Notes

Reaction equation

HRID 1682314 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-c12d3a0dbdcc48729c510c4a4026a48d
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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