Synthesis of succinimidyl-(S)-naproxen ester and its application for indirect enantioresolution of penicillamine by reversed-phase high-performance liquid chromatography.
Synthesis of N-succinimidyl-(S)-2-(6-methoxynaphth-2-yl) propionate was carried out by the reaction of (S)-naproxen with N-hydroxysuccinimide in the presence of dicyclohexyl carbodiimide. It was characterized and was used as a chiral derivatizing reagent, under mild conditions, to form diastereomers of dl-penicillamine which were resolved by reversed-phase high-performance liquid chromatography using triethyl ammonium phosphate buffer (pH 4.0, 5mM)-acetonitrile (linear gradient (30min) of acetonitrile from 30 to 70%). Excellent separation was achieved with gradient mobile phase. The detection limit was at pmol level.
Bhushan
Ravi
R
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, India. rbushfcy@iitr.ernet.in
Tanwar
Shivani
S
D002234:Carbodiimides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004952:Esters; D015394:Molecular Structure; D009288:Naproxen / Q000138:chemical synthesis / Q000737:chemistry*; D010396:Penicillamine / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D015203:Reproducibility of Results; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry
D002234:Carbodiimides; D004952:Esters; D013388:Succinimides; D009288:Naproxen; D010396:Penicillamine; C001426:N-hydroxysuccinimide