Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 89396-94-1, is researched, SMILESS is O=C([C@H](CN1C)N(C([C@@H](N[C@@H](CCC2=CC=CC=C2)C(OCC)=O)C)=O)C1=O)O.[H]Cl, Molecular C20H28ClN3O6Journal, Article, Journal of Pharmaceutical and Biomedical Analysis called Application of quantitative NMR for purity determination of standard ACE inhibitors, Author is Shen, Shi; Yang, Xing; Shi, Yaqin, the main research direction is NMR purity thiol ene click reaction; ACE inhibitors; Captopril; Diastereoisomers; Thiol-ene click reaction; qNMR.Application In Synthesis of (S)-3-((S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1-methyl-2-oxoimidazolidine-4-carboxylic acid hydrochloride.
This study investigated the accuracy of the quant. NMR method for purity determination of ACE inhibitors reference standards and the discovery of two pairs of new diastereoisomers. Six types of ACE inhibitors, imidapril hydrochloride, benazepril hydrochloride, lisinopril, enalapril maleate, quinapril hydrochloride, and captopril were quantificated and validated for the qNMR method by discussing factors that affect parameters of the qNMR experiment, internal standards, integration, pH-effect, and uncertainty. The results were compared with data obtained by the mass balance method. The study found that maleic acid influenced the quantification of captopril in deuteroxide because of a chem. reaction. The mixtures of the reaction products were isolated by HPLC and structurally elucidated by NMR as two pairs of new diastereoisomers, 1-[(2S,4R)-thio-2-methylpropionyl-5-d-ethanedicarboxylicacid]-L-proline and 1-[(2S,4S)-thio-2-methylpropionyl-5-d-ethanedicarboxylicacid]-L-proline. The results showed that the accuracy and precision of quant. 1H NMR spectroscopy satisfied the requirements for quant. anal. of chem. reference standards and provided a simple, rapid, and reliable method for purity determination of ACE inhibitors systematically.
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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”