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

HRID 1913588Notes

Reaction equation

HRID 1913588 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 N-allyl-L-aspartic acid di-tert-butyl ester (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-c9306167bc9344b9845b82b48801019d
Source dataset
uspto-grants-2013_12
Patent number
US08609715B2

Reaction notes

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