Ethyl N-benzyl-N-((tert-butoxycarbonyl)-L-valyl)glycinate → N-benzyl-N-[(S)-valinyl]glycine Ethyl Ester

HRID 1063851노트

반응식

HRID 1063851 반응식
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7](=[O:20])[C@H:8]([CH:17]([CH3:19])[CH3:18])[NH:9]C(OC(C)(C)C)=O)[CH3:2]>Cl.O1CCOCC1>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7](=[O:20])[C@H:8]([CH:17]([CH3:19])[CH3:18])[NH2:9])[CH3:2]

참가 물질

4

반응물 1

HCID 23402347Ethyl N-benzyl-N-((tert-butoxycarbonyl)-L-valyl)glycinate

생성물 1

HCID 23402348N-benzyl-N-[(S)-valinyl]glycine Ethyl Ester수율 97.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5.82 gm (14.8 mMol) N-benzyl-N-[N′-tert-butoxycarbonyl-(S)-valinyl]glycine ethyl ester in 20 mL 4N hydrogen chloride in dioxane was stirred at room temperature under a nitrogen atmosphere over night. The reaction mixture was concentrated under reduced pressure and the residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The aqueous phase was extracted again with dichloromethane. The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure to provide 4.2 gm (97%) of the desired compound as a yellow oil.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. extractionThe aqueous phase was extracted again with dichloromethane
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b5fc385efb4e4fc69df6091e5a439039
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06967201B1

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