Indirect high-performance liquid chromatographic resolution of racemic tertiary amines as their diastereomeric urea derivatives after N-dealkylation

Chemical Reagents and Derivatization Procedures in Drug Analysis

“…(157) Racemic phenothiazines were N -demethylated with vinyl chloroformate to form their secondary amines, which could then be reacted with (R)-(+)-1-phenylethyl isocyanate ( Table 5, reagent 3), and these compounds were separated by reversed-phase HPLC. (158) Tertiary tetrahydroisoquinolines, such as diclofensine, were oxidized before photochemical conversion to fluorescent isoquinolinium derivatives. (159) After postcolumn ion-pair extraction of secoverine, peroxylate chemiluminescence (CL) detection was carried out.…”

Chemical Reagents and Derivatization Procedures in Drug Analysis

“…(157) Racemic phenothiazines were N -demethylated with vinyl chloroformate to form their secondary amines, which could then be reacted with (R)-(+)-1-phenylethyl isocyanate ( Table 5, reagent 3), and these compounds were separated by reversed-phase HPLC. (158) Tertiary tetrahydroisoquinolines, such as diclofensine, were oxidized before photochemical conversion to fluorescent isoquinolinium derivatives. (159) After postcolumn ion-pair extraction of secoverine, peroxylate chemiluminescence (CL) detection was carried out.…”

Vinyl Chloroformate

“…This dealkylation process also is part of an asymmetric synthesis of α-amino esters (eq 8), 12 as well as the key step of a protocol for resolving tertiary amine enantiomers. 13 Also, VOC-Cl-induced dealkylation permits an improved synthesis of the emergency heroin antidote naloxone from oxymorphone (eq 9). 6,14 Vinyl chloroformate largely has been replaced for Ndealkylation by 1-Chloroethyl Chloroformate.…”

Chemical Reagents and Derivatization Procedures in Drug Analysis

“…(157) Racemic phenothiazines were N -demethylated with vinyl chloroformate to form their secondary amines, which could then be reacted with (R)-(+)-1-phenylethyl isocyanate ( Table 5, reagent 3), and these compounds were separated by reversed-phase HPLC. (158) Tertiary tetrahydroisoquinolines, such as diclofensine, were oxidized before photochemical conversion to fluorescent isoquinolinium derivatives. (159) After postcolumn ion-pair extraction of secoverine, peroxylate chemiluminescence (CL) detection was carried out.…”

Vinyl Chloroformate

“…This dealkylation process also is part of an asymmetric synthesis of α-amino esters (eq 8), 12 as well as the key step of a protocol for resolving tertiary amine enantiomers. 13 Also, VOC-Cl-induced dealkylation permits an improved synthesis of the emergency heroin antidote naloxone from oxymorphone (eq 9). 6,14 Vinyl chloroformate largely has been replaced for Ndealkylation by 1-Chloroethyl Chloroformate.…”

Chemical Reagents and Derivatization Procedures in Drug Analysis

“…(157) Racemic phenothiazines were N -demethylated with vinyl chloroformate to form their secondary amines, which could then be reacted with (R)-(+)-1-phenylethyl isocyanate ( Table 5, reagent 3), and these compounds were separated by reversed-phase HPLC. (158) Tertiary tetrahydroisoquinolines, such as diclofensine, were oxidized before photochemical conversion to fluorescent isoquinolinium derivatives. (159) After postcolumn ion-pair extraction of secoverine, peroxylate chemiluminescence (CL) detection was carried out.…”

Vinyl Chloroformate

“…This dealkylation process also is part of an asymmetric synthesis of α-amino esters (eq 8), 12 as well as the key step of a protocol for resolving tertiary amine enantiomers. 13 Also, VOC-Cl-induced dealkylation permits an improved synthesis of the emergency heroin antidote naloxone from oxymorphone (eq 9). 6,14 Vinyl chloroformate largely has been replaced for Ndealkylation by 1-Chloroethyl Chloroformate.…”