Ethyl Acetate → HCID 22493882, compound

HRID 1296209Notes

Reaction equation

HRID 1296209 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH:5]([O:25][CH:26]([CH3:28])[CH3:27])[CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([O:22][CH3:23])=[C:9](Br)[CH:8]=1)[CH3:2].[C-:30]#[N:31].[Na+].C(OCC)(=O)C>C(#N)CC.[Cu](I)I>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([O:25][CH:26]([CH3:28])[CH3:27])[CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([O:22][CH3:23])=[C:9]([C:30]#[N:31])[CH:8]=1)[CH3:2]

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 3(3-bromo-5-[(t-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionic acid ethyl ester was dissolved in 5 ml of propionitrile. 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 nitrogen atmosphere. The reaction mixture was cooled down to room temperature, and ethyl acetate was added thereto. The solution was filtered through Celite, and the filtrate was evaporated. The residue was purified by silica gel column chromatography, to give 586 mg of 3-(3-cyano-5-[(t-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionic acid ethyl ester from fractions eluted with hexane-ethyl acetate (4:1).

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight in nitrogen atmosphere
  3. filtrationThe solution was filtered through Celite
  4. customthe filtrate was evaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-94fa3ff66b3942bfba1ad8b92e2797a4
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Reaction notes

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