Allyl bromide → N-allyl-D-alanine t-butyl ester

HRID 1755826Notes

Reaction equation

HRID 1755826 reaction equation
[C:1]([O:5][C:6](=[O:10])[C@@H:7]([CH3:9])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH2:11](Br)[CH:12]=[CH2:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:10])[C@@H:7]([CH3:9])[NH:8][CH2:13][CH:12]=[CH2:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 7359212tert-butyl (2R)-2-aminopropanoate

Product 1

HCID 54332184N-allyl-D-alanine t-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

D-Alanine t-butylester (68) is treated with one equivalent allyl bromide and one equivalent of triethylamine in toluene under reflux. The solvent is evaporated and the product is purified by flash chromatography on silica gel to give (69).

Workup

  1. temperatureunder reflux
  2. customThe solvent is evaporated
  3. customthe product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-48efffad11d94dafa55ea06d132ab9b7
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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