Allyl bromide → N-allyl-L-aspartic acid di-tert-butyl ester

HRID 529207Notes

Reaction equation

HRID 529207 reaction equation
Cl.[C:2]([O:6][C:7](=[O:18])[C@H:8]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>C(#N)C>[C:2]([O:6][C:7](=[O:18])[C@H:8]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[NH:9][CH2:27][CH:26]=[CH2:25])([CH3:4])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13768146L-Aspartic acid, bis(1,1-dimethylethyl) ester, hydrochloride

Product 1

HCID 86673330N-allyl-L-aspartic acid di-tert-butyl esterYield 52.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

L-Aspartic acid di-tert-butyl ester hydrochloride (1.0 g, 3.5 mmol) was dissolved in acetonitrile (7 mL), potassium carbonate (0.98 g, 7.1 mmol) and allyl bromide (0.29 mL, 3.4 mmol) were added, and the mixture was stirred at room temperature overnight. The insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5) to give the title compound (0.50 g, 1.8 mmol).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-9970a7f4e60a4d999ebdcf6b84c3d1ba
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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