物理化学学报 >> 2002, Vol. 18 >> Issue (09): 821-824.doi: 10.3866/PKU.WHXB20020911

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光活性酮咯酸衍生物的拆分及绝对构型的测定

宁家成;杨鳌;关烨第;王哲明;严纯华   

  1. 北京大学化学与分子工程学院; 北京大学稀土材料化学与应用国家重点实验室，北京　100871
  • 收稿日期:2002-01-15 修回日期:2002-02-10 发布日期:2002-09-15
  • 通讯作者: 关烨第 E-mail:gyedi@chem.pku.edu.cn

The Resolution of the Optical Active Derivatives of Ketorolac and the Determination of its Absolute Configuration

Ning Jia-Cheng;Yang Ao;Guan Ye-Di;Wang Zhe-Ming;Yan Chun-Hua   

  1. College of Chemistry and Molecular Engineering; Peking University; State Key Laboratory of Rare Earth Materials Chemistry and Applications, Peking University，Beijing　100871
  • Received:2002-01-15 Revised:2002-02-10 Published:2002-09-15
  • Contact: Guan Ye-Di E-mail:gyedi@chem.pku.edu.cn

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摘要： 酮咯酸与L-脯氨酸苄酯在缩合剂作用下形成酰胺，用柱层析分离了一对非对映异构体并进行了表征.用单晶X衍射测定了酮咯酸脯氨酸苄酯酰胺一个异构体的晶体结构，并用内参法确定了其绝对构型.晶体属正交晶系，空间群P212121，晶胞参数a=0.896 45（1）nm，b=1.271 23（2）nm，c=2.076 21（4）nm， V=2.366 04（6）nm3，Z=4，最终偏离因子R1=0.046 4.

关键词: 酮咯酸, 酰胺, 非对映异构体, 拆分, 晶体结构, 绝对构型

Abstract: A pair of diastereoisomer of Pro-Obzl of keterolac amide, formed by the reaction of(±)-ketorolac and L-proline under the action of condensation agent, were resolved using column chromatography and characterized by 1H NMR, 13C NMR, IR, MS spectra and elemental analysis. The crystal structure of one diastereoisomer of the amides was determined by single crystal diffraction analysis, and the absolute configuration of which was deduced by internal reference. The crystal belongs to orthorhombic space group P212121. Crystallographic data are:a=0.896 45(1)nm, b=1.271 23(2)nm, c=2.076 21(4)nm, V=2.366 04(6)nm3, Z=4, R1=0.0464.

Key words: Ketorolac, Amide, Diastereoisomer, Resolution, Crystal structure, 　Absolute configuration