Methane → HCID 86742128, compound

HRID 649671Notes

Reaction equation

HRID 649671 reaction equation
O=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[C:9]([O:12][CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])(=[O:11])[CH3:10].C>O1CCOCC1>[N-:15]=[C:4]=[O:3].[CH3:2][O:17][C:16](=[O:18])[C@H:14]([CH2:13][O:12][C:9](=[O:11])[CH3:10])[NH2:15]

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 99478O-Acetyl-L-serine

Product 1

HCID 86742128HCID 86742128, 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 O-acetylserine 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 O-acetylserine 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-9489414a29df4bd7a47accc8cb5245fb
Source dataset
uspto-grants-1988_04
Patent number
US04740611

Reaction notes

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