5560-77-0Relevant academic research and scientific papers
Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase
Hellinghausen, Garrett,Lopez, Diego A.,Lee, Jauh T.,Wang, Yadi,Weatherly, Choyce A.,Portillo, Abiud E.,Berthod, Alain,Armstrong, Daniel W.
, p. 1067 - 1078 (2018/08/01)
A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.
Asymmetric synthesis method for anti-allergy drug carbinoxamine
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, (2017/07/21)
The invention relates to an asymmetric synthesis method for an anti-allergy drug carbinoxamine. The method specifically comprises the following steps: oxidizing (4-chlorophenyl)(2-pyridyl)ketone to obtain (4-chlorophenyl)(2-pyridyl)ketone-N-oxide; by taking monosulfonylated chiral diamine and metal ruthenium/rhodium/iridium complex as catalysts and sodium formate or a formic acid and triethylamine mixture or isopropanol as a hydrogen source, reducing the (4-chlorophenyl)(2-pyridyl)ketone-N-oxide through asymmetry transfer hydrogenation to prepare (S)-(4-chlorophenyl)(2-pyridyl)methanol-N-oxide; reducing the (S)-(4-chlorophenyl)(2-pyridyl)methanol-N-oxide to obtain (S)-(4-chlorophenyl)(2-pyridyl)methanol; and performing etherification reaction on the (S)-(4-chlorophenyl)(2-pyridyl)methanol and 2-chloro-N,N-dimethylethylamine to obtain the product, wherein the overall yield is 74.6%.
Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction
Corey,Helal, Christopher J.
, p. 5675 - 5678 (2007/10/03)
A new process has been developed for the highly enantioselective catalytic reduction of 2-aroylpyridines and successfully applied to the synthesis of (S)-carbinoxamine (1), a therapeutically important histamine H1 antagonist. Related enantioselective reductions of 4-aroylpyridines and ortho-substituted benzophenones are also described.
