title: Analytical and semi-preparative HPLC enantioseparation of novel pyridazin-3(2H)-one derivatives with α-aminophosphonate moiety using immobilized polysaccharide chiral stationary phases.
abstract: The direct HPLC enantioseparation of a novel series of chiral pyridazin-3(2H)-one derivatives with α-aminophosphonate moiety was performed on two immobilized polysaccharide chiral stationary phases (Chiralpak IA, Chiralpak IC) using n-hexane (n-Hex)/dichloromethane (DCM) mobile phase with 5% alcohol additive. Good baseline separation of the enantiomers was achieved using amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak IA) on analytical scale. The analytical method was further scaled up to semi-preparative loading to obtain small amounts of both the enantiomers of pyridazin-3(2H)-one derivative. The semi-preparative resolution of all compounds was successfully achieved with n-hexane/dichloromethane/ethanol (EtOH) as mobile phase using a semi-preparative Chiralpak IA column. The first fractions were isolated with purities of >99.9% (enantiomeric excess (e.e.), and the second fractions were obtained with purities of >98.2% (enantiomeric excess). The assignment of the absolute configuration was established for the F1 fraction of compound a-2 by single-crystal X-ray diffraction method.
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Center for Research and Development of Fine Chemicals, Ministry of Education, Guizhou University, Guiyang, PR China.
authors.forename: Yuping
authors.initials: Y
authors.lastname: Zhang
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Zhang
authors.forename: Jun
authors.initials: J
authors.lastname: Zhou
authors.forename: Baoan
authors.initials: B
authors.lastname: Song
authors.forename: Pinaki S
authors.initials: PS
authors.lastname: Bhadury
authors.forename: Deyu
authors.initials: D
authors.lastname: Hu
authors.forename: Song
authors.initials: S
authors.lastname: Yang
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D015394:Molecular Structure; D011134:Polysaccharides / Q000737:chemistry; D011724:Pyridazines / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism
chemical_list: D011134:Polysaccharides; D011724:Pyridazines