Methane → HCID 86741876, compound

HRID 649674Notes

Reaction equation

HRID 649674 reaction equation
O=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[C:9]([O:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[NH2:19])=[CH:15][CH:14]=1)(=[O:11])[CH3:10].C>O1CCOCC1>[N-:19]=[C:4]=[O:3].[CH3:2][O:21][C:20](=[O:22])[C@H:18]([CH2:17][C:16]1[CH:23]=[CH:24][C:13]([O:12][C:9](=[O:11])[CH3:10])=[CH:14][CH:15]=1)[NH2:19]

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 14214355HCID 14214355, compound

Product 1

HCID 86741876HCID 86741876, 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-acetyltyrosine 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 fractionally distilled to give O-acetyltyrosine 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 fractionally distilled

Sources & evidence

ORD record
ord-e10ac4aabda348cfa251c646eaba0826
Source dataset
uspto-grants-1988_04
Patent number
US04740611

Reaction notes

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