Ethanol → HCID 54435014, compound

HRID 376147Notes

Reaction equation

HRID 376147 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([NH:23]C=O)[CH:6]=[C:7]([CH2:12][P:13]([O:19]C(C)C)([O:15]C(C)C)=[O:14])[CH2:8][O:9][CH2:10][CH3:11])[CH3:2].C[SiH](C)C.C(O)C>ClCCl>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([NH2:23])[CH:6]=[C:7]([CH2:12][P:13]([OH:15])([OH:19])=[O:14])[CH2:8][O:9][CH2:10][CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 70435TrimethylsilaneHCID 54468930HCID 54468930, compound

Product 1

HCID 54435014HCID 54435014, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.10 g (2.8 mmol) of 5-ethoxy-4-diisopropylphosphonomethyl-2-formylamino-pent-3-enoic acid ethyl ester are dissolved in 20 ml of dichloromethane, and 1.6 ml (12.3 mmol) of trimethylsilane are added dropwise at room temperature. The mixture is left to stand at room temperature for 7 hours, 20 ml of ethanol are added, the mixture is left to stand for a further 15 hours and is concentrated by evaporation, the residue is dissolved in 10 ml of ethanol, and a mixture of 10 ml of propylene oxide and 10 ml of ethanol is added dropwise. A suspension forms, which is stirred at room temperature for 2 hours and is then filtered with suction. Drying yields 5-ethoxy-2-amino-4-phosphonomethyl-pent-3-enoic acid ethyl ester having a melting point of 217°-218° C. (decomp.).

Workup

  1. waitThe mixture is left
  2. waitthe mixture is left
  3. waitto stand for a further 15 hours
  4. concentrationis concentrated by evaporation
  5. dissolutionthe residue is dissolved in 10 ml of ethanol
  6. additiona mixture of 10 ml of propylene oxide and 10 ml of ethanol
  7. additionis added dropwise
  8. filtrationis then filtered with suction
  9. customDrying

Sources & evidence

ORD record
ord-0df00699d9cc404d8f3bda164394e83a
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

Loading…