Methane → HCID 86741872, compound

HRID 649668Notes

Reaction equation

HRID 649668 reaction equation
O=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[NH2:9][C@H:10]([C:15]([OH:17])=[O:16])[C@H:11]([CH2:13][CH3:14])[CH3:12].C>O1CCOCC1>[N-:9]=[C:4]=[O:3].[CH3:2][O:16][C:15](=[O:17])[C@H:10]([C@H:11]([CH2:13][CH3:14])[CH3:12])[NH2:9]

Participants

5

Reactant 3

HCID 297MethaneHCID 6306L-IsoleucineHCID 10426Diphosgene

Product 1

HCID 86741872HCID 86741872, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.35 mol diphosgene is added dropwise over 1 hour to a mixture of 0.28 mol of the methyl ester of isoleucine and 0.4 g activated charcoal in 400 mL dioxane under N2. The reaction mixture is then heated and stirred at reflux for 21/2 hours. The reaction mixture is then cooled, filtered, and concentrated to dryness by rotary evaporator, keeping exposure to moisture to a minimum. The crude product is re-dissolved in 100 mL THF, and the pH of the solution is adjusted to 5.5-6.0 by addition of pyridine. The product mixture is again filtered, and the filtrate is fractionally distilled to give isoleucine methyl ester isocyanate.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux for 21/2 hours
  3. temperatureThe reaction mixture is then cooled
  4. filtrationfiltered
  5. concentrationconcentrated to dryness by rotary evaporator
  6. dissolutionThe crude product is re-dissolved in 100 mL THF
  7. additionthe pH of the solution is adjusted to 5.5-6.0 by addition of pyridine
  8. filtrationThe product mixture is again filtered
  9. distillationthe filtrate is fractionally distilled

Sources & evidence

ORD record
ord-e118e73c520e4f318c5fdf9ee49e4760
Source dataset
uspto-grants-1988_04
Patent number
US04740611

Reaction notes

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