Ethyl Acetate → HCID 86627815, compound

HRID 2425454Notes

Reaction equation

HRID 2425454 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][NH:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(OCC)(=O)C>C(#N)C>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][N:5]([CH3:6])[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 79177tert-Butyl bromoacetate

Product 1

HCID 86627815HCID 86627815, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N,N,N′-trimethylethylenediamine (899 mg, Tokyo Kasei Kogyo) in acetonitrile (31 ml) was cooled to 0° C., added with potassium carbonate (2.21 g, and then slowly added dropwise with tert-butyl bromoacetate (1.56 g, Wako Pure Chemical Industries), and the mixture was stirred at the same temperature for 12 hours. The reaction mixture was added with ethyl acetate, and the insoluble solids were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (methanol:chloroform=1:10) to obtain the title compound (1.25 g).

Workup

  1. customthe insoluble solids were removed by filtration through Celite
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (methanol:chloroform=1:10)

Sources & evidence

ORD record
ord-29b2bc50691949c6941a272b351fb567
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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