Sodium Bicarbonate → HCID 131723835, compound

HRID 1264179Notes

Reaction equation

HRID 1264179 reaction equation
Cl.CO[C:4](=O)[C@@H:5]([CH2:8][SH:9])[NH:6][CH3:7].Br[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.[C:23](=[O:26])(O)[O-:24].[Na+]>CN(C=O)C>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][N:6]([CH2:7][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[C@@:5]([CH3:4])([C:23]([OH:24])=[O:26])[CH2:8][SH:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 124174182-(Bromomethyl)quinolineHCID 87930388HCID 87930388, compound

Product 1

HCID 131723835HCID 131723835, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The ligand N,N-bis[(2-quinolyl)methyl]-(S)-methly-L-cysteine was prepared from the dropwise addition of (S)-methyl-L-cysteine methylester hydrochloride (2.0 g, 10.8 mmol) in 10 mL DMF to a stirring solution of 2-bromomethylquinoline (4.8 g, 21.6 mmol) and sodium bicarbonate (4.1 g, 49 mmol) in 40 mL. The mixture was allowed to react for 4 h at 80° C. Evaporation of the solvent followed by column chromatography with 3:1 hexancs: ethyl acetate (Rf 0.3) afforded the ester of the ligand (1.7 g, 82%). Saponification was achieved by stirring the ester (1.9 g, 4.4 mmol) in 8 mL THF with LiOH(4.6 mL, 1 M) for 2.5 h. The solution was then extracted with methylene chloride, and the aqueous layer acidified with 0.5 M HClO4 to pH 6. Several extractions with methylene chloride followed by drying and evaporation of the solvent afforded the crude acid. Purification by column chromatography with ethyl acetate afforded the pure ligand (0.57 g, 31%).

Workup

  1. customto react for 4 h at 80° C
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2e3357b2c48e424e8fe26f3944f4c60e
Source dataset
uspto-grants-2003_04
Patent number
US06541645B1

Reaction notes

Loading…