Methane → Asparagine methyl ester isocyanate

HRID 247213

반응식

HRID 247213 반응식
[O:1]=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[NH2:9][C@H:10](C(O)=O)[CH2:11][C:12](=[O:14])[NH2:13].C>O1CCOCC1>[N-:13]=[C:12]=[O:14].[CH3:4][O:3][C:2](=[O:1])[C@H:10]([CH2:11][C:12](=[O:14])[NH2:13])[NH2:9]

참가 물질

5

반응물 3

HCID 297MethaneHCID 6267(-)-AsparagineHCID 10426Diphosgene

생성물 1

HCID 86741878Asparagine methyl ester isocyanate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

0.35 mol diphosgene is added dropwise over 1 hour to a mixture of 0.28 mol of the methyl ester of asparagine 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 asparagine methyl ester isocyanate.

후처리

  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

출처 및 근거

ORD 기록
ord-44921723b7b74232a6e687ac4c5d88c4
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04705864

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