使用手性镧系螯合物通过质子核磁共振光谱法测定茚达立酮的光学纯度。

Determination of the optical purity of indacrinone by proton nuclear magnetic resonance spectroscopy using chiral lanthanide chelates.

作者信息

Hanna G M, Lau-Cam C A

机构信息

Food and Drug Administration, Department of Health and Human Services, New York Regional Laboratory, Brooklyn 11239-1593.

出版信息

J Pharm Biomed Anal. 1989;7(8):919-28. doi: 10.1016/0731-7085(89)80016-0.

DOI:10.1016/0731-7085(89)80016-0

PMID:2562290

Abstract

A simple, specific and reliable 1H-NMR spectroscopic method for the quantitative determination of the optical purity of indacrinone is described. After conversion of the S(+)- and R(-)-enantiomers to their methyl ester derivatives, they were coordinated with chiral europium(III) or praseodymium(III) shift reagents in CCl4/C2HCl3 (2:1). The optical purity was calculated from the relative intensities of the enantiomeric resonance signals for the protons of the methyl groups at position C(2) of the indanone ring. Mean +/- SD (n = 6) recoveries of S(+)-indacrinone from synthetic enantiomeric mixtures amounted to 99.75 +/- 0.63% when using europium(III) and 100.01 +/- 0.55% when using praseodymium(III).

摘要

描述了一种用于定量测定茚达立酮光学纯度的简单、特异且可靠的¹H-NMR光谱法。将S(+)-和R(-)-对映体转化为它们的甲酯衍生物后，使其在CCl₄/C₂HCl₃（2:1）中与手性铕(III)或镨(III)位移试剂配位。根据茚满酮环C(2)位甲基质子的对映体共振信号的相对强度计算光学纯度。当使用铕(III)时，从合成对映体混合物中回收S(+)-茚达立酮的平均回收率±标准差（n = 6）为99.75±0.63%，使用镨(III)时为100.01±0.55%。