Water → 2-{4-Methoxy-2-[(3-{[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}quinoxalin-2-yl)amino]phenyl}ethyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

Participants

Reaction Steps

To a suspension of N-(3-{[2-(2-hydroxyethyl)-5-methoxyphenyl]amino}quinoxalin-2-yl)-1-methyl-1H-imidazole-4-sulfonamide (200 mg; 0.44 mmol; 1 eq), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (92.8 mg; 0.48 mmol; 1.1 eq) and N,N-dimethylpyridin-4-amine (59 mg; 0.48 mmol; 1.1 eq) in a mixture of DCM (10 mL) and DMF (1 mL) is added fmoc-l-valine (164 mg; 0.48 mmol; 1.1 eq). The reaction mixture is stirred for 18 h at room temperature. Water is added and organic phase is washed several times with 10% citric acid then dried under MgSO4. The solvent is removed under reduced pressure and residue purified by flash chromatography using EtOAc as eluent to afford 200 mg (59%) of the title compound as a yellow gum. HPLC (max plot) 98%; Rt 5.46 min. LC/MS: (ES+): 775.7, (ES−): 773.9.

Provenance & Evidence