Ethyl Acetate → HCID 22493882, compound

HRID 1816601Notes

Reaction equation

HRID 1816601 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:19][CH:20]([O:26][CH:27]([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:5]=[C:6]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=1[O:8][CH3:9].[C-:30]#[N:31].[Na+].C(OCC)(=O)C>C(#N)CC.[Cu](I)I>[C:30]([C:2]1[CH:3]=[C:4]([CH2:19][CH:20]([O:26][CH:27]([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:5]=[C:6]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=1[O:8][CH3:9])#[N:31]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 22494028HCID 22494028, compound

Product 1

HCID 22493882HCID 22493882, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 7854PropionitrileSolvent

Procedure

876 mg of ethyl 3-(3-bromo-5-[(tertiary butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionate was dissolved in 5 ml propionitrile, and 182 mg of sodium cyanide, 214 mg of tetrakistriphenylphosphine palladium and 70 mg of copper iodide were added, followed by heating under reflux overnight in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, ethyl acetate was added thereto and filtered through Celite. The filtrate was evapoarated and the residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (4:1), 586 mg of ethyl 3-(3-cyano-5-[(tertiary butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionate was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight in a nitrogen atmosphere
  3. filtrationfiltered through Celite
  4. customthe residue was purified by silica gel column chromatography
  5. washfrom fractions eluted with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-410550954f1346e8813d297c53da5af7
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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