Methane → HCID 86742130, compound

HRID 649672Notes

Reaction equation

HRID 649672 reaction equation
[C:1]([O:4][C@H:5]([CH3:11])[C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7])(=[O:3])[CH3:2].C.[O:13]1[CH2:18]COC[CH2:14]1>>[N-:7]=[C:18]=[O:13].[CH3:14][O:9][C:8](=[O:10])[C@H:6]([C@@H:5]([CH3:11])[O:4][C:1](=[O:3])[CH3:2])[NH2:7]

Participants

4

Reactant 3

HCID 297MethaneHCID 312751,4-DioxaneHCID 16718064O-Acetyl-L-threonine

Product 1

HCID 86742130HCID 86742130, compound

Procedure

0.35 mol disphogene is added dropwise over 1 hour to a mixture of 0.28 mol of the methyl ester of O-acetylthreonine 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-acetylthreonine 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-b11ac5b2926442ae90c029d196dd643b
Source dataset
uspto-grants-1988_04
Patent number
US04740611

Reaction notes

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