Potassium Iodide → L82Nub8C3A

HRID 2076382Notes

Reaction equation

HRID 2076382 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-708d8136c76344048ed579e953d5def5
Source dataset
uspto-grants-2011_04
Patent number
US07923567B2

Reaction notes

Loading…