Methane → HCID 86744417, compound

HRID 1111038Notes

Reaction equation

HRID 1111038 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[CH2:9]([O:12][C:13](=[O:23])[C@H:14]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH2:15])[CH:10]=[CH2:11].C>O1CCOCC1>[N-:15]=[C:4]=[O:3].[CH2:9]([O:12][C:13](=[O:23])[C@H:14]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:15])[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 297MethaneHCID 10426DiphosgeneHCID 10904926HCID 10904926, compound

Product 1

HCID 86744417HCID 86744417, 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 phenylalanine allyl ester, prepared as described by H. Waldmann and H. Kunz in Liebigs Ann. Chem., 1983, 1712-1725, 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 product is purified by fractional distillation to give phenylalanine allyl ester isocyanate.

Workup

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

Sources & evidence

ORD record
ord-d828a462041544c992eb42ddb34bb0dd
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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