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

HRID 1063851Notes

Reaction equation

HRID 1063851 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b5fc385efb4e4fc69df6091e5a439039
Source dataset
uspto-grants-2005_11
Patent number
US06967201B1

Reaction notes

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