Hydrochloric Acid → HCID 86745096, compound

HRID 728883Notes

Reaction equation

HRID 728883 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([NH:19]C=O)/[CH:5]=[C:6](/[CH2:10][P:11]([O:16]CC)([O:13]CC)=[O:12])\[CH2:7][CH:8]=[CH2:9].C[Si](C)(C)I.S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>ClCCl.C(O)C>[NH2:19][CH:4](/[CH:5]=[C:6](/[CH2:10][P:11]([OH:16])([OH:13])=[O:12])\[CH2:7][CH:8]=[CH2:9])[C:3]([OH:22])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 86745095HCID 86745095, compound

Product 1

HCID 86745096HCID 86745096, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

0.74 g of E-2-formylamino-4-diethylphosphonomethyl-3,6-heptadienoic acid methyl ester is dissolved in 12 ml of dichloromethane, and 0.7 ml of trimethyliodosilane is added dropwise thereto. After stirring at room temperature for 4 hours, 1N sodium thiosulphate solution is added until the colour of the reaction solution becomes lighter. 10 ml of a 4.5N hydrochloric acid solution are then added to the reaction mixture, which is then stirred at room temperature for 30 minutes. The aqueous phase is separated off, washed twice with 20 ml of dichloromethane each time, and concentrated by evaporation in vacuo. The residue is dissolved in 10 ml of4.5N hydrochloric acid, stirred at room temperature for 16 hours, and then concentrated by evaporation in vacuo. The residue so obtained is taken up in 40 ml of ethanol and filtered until clear, and then 10 ml of propylene oxide/ethanol (1:1) are added dropwise. The resulting white precipitate isfiltered off and purified by column chromatography (Dowex 50×8/H2O). Concentration yields E-2-amino-4-phosphonomethyl-3,6-heptadienoic acid in the form of a white crystallisate, m.p. 154°-157°, 1H-NMR (D2O): 2.64 (d, 2H, P--CH2); 3.15 (m, 2H, C(5)--H); 5.20 (m, 2H, C(7)--H); 5.50 (dd, 1 H, C(3)--H); 5.90 (m, 1 H, C(6)--H).

Workup

  1. stirringis then stirred at room temperature for 30 minutes
  2. customThe aqueous phase is separated off
  3. washwashed twice with 20 ml of dichloromethane each time
  4. concentrationconcentrated by evaporation in vacuo
  5. dissolutionThe residue is dissolved in 10 ml of4
  6. stirring5N hydrochloric acid, stirred at room temperature for 16 hours
  7. concentrationconcentrated by evaporation in vacuo
  8. customThe residue so obtained
  9. filtrationfiltered until clear, and then 10 ml of propylene oxide/ethanol (1:1)
  10. additionare added dropwise
  11. custompurified by column chromatography (Dowex 50×8/H2O)
  12. concentrationConcentration

Sources & evidence

ORD record
ord-e1e3ec17a2c643498a5f581859dba424
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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