Potassium Iodide → L82Nub8C3A

HRID 18844

Reaction equation

HRID 18844 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.[CH3:17][O:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:24])[CH3:23])[NH2:21].[C:26](=[O:29])([O-:28])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[C:19]([OH:25])(=[O:18])[C:26]([OH:28])=[O:29].[CH3:17][O:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:24])[CH3:23])[NH:21][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 94285Valine methyl esterHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 51050401L82Nub8C3A

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
42.5 °C

Procedure

In one of the preferred embodiments 4-bromomethyl-2′-cyanobiphenyl, L-valine methyl ester, potassium carbonate and potassium iodide are taken in acetonitrile. The reaction mixture was stirred at about 40-45° C. for about 3 to 4 hours and the solvent was removed under vacuum. Water and xylene was added to reaction mass and the organic layer was separated. A solution of oxalic acid was added to the organic layer and stirred for about an hour at ambient temperature to give N-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester oxalate salt.

Workup

  1. customthe solvent was removed under vacuum
  2. additionWater and xylene was added to reaction mass
  3. customthe organic layer was separated
  4. additionA solution of oxalic acid was added to the organic layer
  5. stirringstirred for about an hour at ambient temperature

Sources & evidence

ORD record
ord-d17d76d5bf9d49e0bd43c815da86fdef
Source dataset
uspto-grants-2010_06
Patent number
US07741507B2

Linked notes

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