Trimethylsilyl iodide → HCID 86742182, compound

HRID 1252996Notes

Reaction equation

HRID 1252996 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][C@@H:9]([NH:11][C:12](=[O:20])[CH2:13][P:14]([O:18]C)([O:16]C)=[O:15])[CH2:8][CH2:7][NH:6]1)=[O:4].C[Si](I)(C)C>C(Cl)Cl>[P:14]([CH2:13][C:12]([NH:11][C@H:9]1[CH2:8][CH2:7][NH:6][C@@H:5]([C:3]([OH:4])=[O:2])[CH2:10]1)=[O:20])([OH:16])([OH:18])=[O:15]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86742183HCID 86742183, compound

Product 1

HCID 86742182HCID 86742182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 900 mg of cis-2-methoxycarbonyl-4-(α-dimethylphosphonoacetamido)-piperidine and 20 ml of methylene chloride is treated with 4 g trimethylsilyl iodide and the resulting mixture is stirred for 16 hours at room temperature. After removal of solvent the residue is stirred with water for 15 minutes and the solvent is removed in vacuo. A solution of the residue in 30 ml of 3N hydrochloric acid is heated under reflux for one hour and evaporated to dryness. A solution of the residue in 15 ml ethanol is treated with 1 ml of propylene oxide. Evaporation to dryness yields cis-4-(α-phosphonoacetamido)-piperidine-2-carboxylic acid.

Workup

  1. customAfter removal of solvent the residue
  2. stirringis stirred with water for 15 minutes
  3. customthe solvent is removed in vacuo
  4. temperatureA solution of the residue in 30 ml of 3N hydrochloric acid is heated
  5. temperatureunder reflux for one hour
  6. customevaporated to dryness
  7. additionA solution of the residue in 15 ml ethanol is treated with 1 ml of propylene oxide
  8. customEvaporation to dryness

Sources & evidence

ORD record
ord-e0cb8529d8f54b559070a49a4a261802
Source dataset
uspto-grants-1988_05
Patent number
US04746653

Reaction notes

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