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

HRID 1063851ノート

反応式

HRID 1063851 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b5fc385efb4e4fc69df6091e5a439039
出典データセット
uspto-grants-2005_11
特許番号
US06967201B1

反応ノート

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