Acetic-formic anhydride → Ethyl N-formyl-3-nitriloalaninate

HRID 408832노트

반응식

HRID 408832 반응식
[N:1]#[C:2][C@@H:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:4].[CH:10](OC(=O)C)=[O:11]>CCOCC>[CH:10]([NH:4][C@H:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:2]#[N:1])=[O:11]

참가 물질

4

반응물 2

HCID 75269Acetic-formic anhydrideHCID 931182Ethyl 3-nitriloalaninate

생성물 1

HCID 86619658Ethyl N-formyl-3-nitriloalaninate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Ethyl 3-nitriloalaninate (26.9 g, 210 mmol) is dissolved in anhydrous ether (200 mL), and cooled in an ice/water bath. Acetic formic anhydride (prepared as a mixture as described above) is added dropwise. When the addition is finished, the reaction mixture is allowed to warm to RT and stirred at RT overnight. Most volatiles are removed in vacuo, and the residue solvents are removed by co-evaporation with toluene (100 mL×4). The red oil obtained precipitates upon scratching in ether, and the resulting solids are recrystallized in ether to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) 8.32 (1H, s), 7.26 (1H, s), 6.46 (1H, bs,), 5.56 (1H, d, J 7.8), 4.39 (2H, q), 1.37 (3H, t).

후처리

  1. temperaturecooled in an ice/water bath
  2. additionis added dropwise
  3. additionWhen the addition
  4. customMost volatiles are removed in vacuo
  5. customthe residue solvents are removed by co-evaporation with toluene (100 mL×4)
  6. customThe red oil obtained
  7. customprecipitates
  8. customthe resulting solids are recrystallized in ether

출처 및 근거

ORD 기록
ord-0270187474e2403883756160bcbfc74f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759361B2

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