High-performance liquid chromatographic resolution of enantiomers of 1-phenyl-2-aminopropanes (amphetamines) with four chiral reagents.
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 ), (-)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride ( MTPA X Cl), 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate ( GITC ), and 2,3,4-tri-O-acetyl-alpha-D- arabinopyranosyl isothiocyanate ( AITC ). Reactions were accomplished under mild conditions (25-70 degrees 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 (C18) 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 .
D000662:Amphetamines / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D003485:Cyanates; D007202:Indicators and Reagents; D017953:Isocyanates; D007536:Isomerism; D017879:Isothiocyanates; D010648:Phenylacetates; D013861:Thiocyanates
D000662:Amphetamines; D003485:Cyanates; D007202:Indicators and Reagents; D017953:Isocyanates; D017879:Isothiocyanates; D010648:Phenylacetates; D013861:Thiocyanates; C041943:2,3,4,6-tetra-O-acetylglucopyranosylisothiocyanate; C020790:phenylethyl isocyanate; C014087:(-)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride; C041942:2,3,4-tri-O-acetylarabinopyranosyl isothiocyanate