Abstract
High-performance liquid chromatography (HPLC) was employed for resolution of enantiomers of chiral ring-substituted 1-phenyl-2-aminopropanes (amphetamines) and 1-phenylethylamine following derivatization with four chiral reagents: ( R)-(+)-1-phenylethyl isocyanate (PEIC), (−)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride (MTPA · Cl), 2,3,4,6-tetra-O-acetyl-β- d-glucopyranosyl isothiocyanate (GITC), and 2,3,4-tri-O-acetyl-α- d-arabinopyranosyl isothiocyanate (AITC). Reactions were accomplished under mild conditions (25–70°C) and were complete for all substrates within 60 min. Derivatization with the sugar isothiocyanates (GITC and AITC) and the acyl chloride (MTPA · Cl) was carried out in methylene chloride or acetonitrile in the presence of a base catalyst while derivatization with the isocyanate (PEIC) was performed in methylene chloride. The diastereomeric derivatives were separated by reversed-phase HPLC (C 18) with a methanol—water mobile phase. In general, HPLC resolution of the diastereomeric reaction products of GITC or AITC, and MTPA · Cl with the amine substrates was more complete (usually greater than 98% baseline separation) than HPLC resolution of the diastereomeric reaction products of PEIC.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of Chromatography B: Biomedical Sciences and Applications
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
