Dimethylformamide → N-Boc-allylglycine methyl ester

HRID 413356Notes

Reaction equation

HRID 413356 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4](OC(=O)C)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CN(C=O)C.[CH2:23](Br)[CH:24]=[CH2:25]>Cl.CCCCCC.CCOC(C)=O.[Zn]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]([CH2:25][CH:24]=[CH2:23])[C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 10922855Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester

Product 1

HCID 22243128N-Boc-allylglycine methyl ester

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester (Ref. Tetrahedron Lett. 1994, 35 3669, 21.1 g, 85.7 mmol), zinc (11.2 g, 171.42 mmol) and DMF (100 mL) at 0° C. is added allylbromide (14.8 mL, 171.4 mmol) dropwise. The reaction is warmed to room temperature and stirred overnight. The mixture is diluted with 0.1N HCl and hexane/EtOAc (2:1), filtered, the reaction mixture is then extracted three times with hexane/EtOAc (2:1). The combined EtOAc layer is washed twice with 0.1 N HCl, brine/H2O, brine, dried over MgSO4, and concentrated under reduced pressure to give an oil.

Workup

  1. filtrationfiltered
  2. extractionthe reaction mixture is then extracted three times with hexane/EtOAc (2:1)
  3. washThe combined EtOAc layer is washed twice with 0.1 N HCl, brine/H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil

Sources & evidence

ORD record
ord-7d5bc69fec7b4c38a101a63584f1b01b
Source dataset
uspto-grants-2003_05
Patent number
US06566381B1

Reaction notes

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