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首页> 外文期刊>RSC Advances >Ring-locking strategy facilitating determination of absolute optical purity of 2-amino-1-butanol by reverse-phase high-performance liquid chromatography
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Ring-locking strategy facilitating determination of absolute optical purity of 2-amino-1-butanol by reverse-phase high-performance liquid chromatography

机译：反相高效液相色谱有助于测定2-氨基-1-丁醇绝对光学纯度的锁环策略

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摘要

A concise and efficient reverse-phase high-performance liquid chromatography (RPLC) method has been established for absolute optical purity assay of 2-amino-1-butanol, which is an important synthetic intermediate of various drugs. Its enantiomers were derivatized with methyl (5-fluoro-2,4-dinitro-phenyl)-(S)-prolinate, which could be regarded as a structural variant of Marfey's reagent. The resultant diastereomers were further cyclized using bis(trichloromethyl)carbonate to form oxazolidin-2-one ring, leading to a distinct difference in their electronic circular dichroism (ECD) spectra. Time-dependent density functional theory (TDDFT) was then applied to simulate theoretical ECD spectra for unambiguous absolute configuration assignment of cyclized products without putative samples. Both pairs of diastereomers could be separated on a reverse-phase C18 column using a mobile phase of methanol or acetonitrile and water with UV detection at 336 nm. The tandem reactions could be integrated into one-pot synthesis with high yield. Thus, exact absolute optical purity of 2-amino-1-butanol could be directly determined by monitoring the peak ratios of these diastereomers. This method is well worth extending to the absolute optical purity assessment of other chiral amino alcohols.
机译：建立了一种简洁高效的反相高效液相色谱（RPLC）方法，用于2-氨基-1-丁醇的绝对光学纯度测定，2-氨基-1-丁醇是各种药物的重要合成中间体。它的对映体是用（5-氟-2,4-二硝基-苯基）-（ S ）-脯氨酸甲酯衍生的，可以认为是Marfey试剂的结构变体。生成的非对映异构体进一步使用碳酸二（三氯甲基）酯环化形成恶唑烷-2-酮环，从而导致其电子圆二色性（ECD）光谱存在明显差异。然后，采用时变密度泛函理论（TDDFT）来模拟理论ECD光谱，以对没有推定样品的环化产物进行明确的绝对构型分配。可以使用甲醇或乙腈和水的流动相在反相C18色谱柱上分离两对非对映异构体，并在336 nm处进行UV检测。串联反应可以高产率地整合到一锅法合成中。因此，可以通过监测这些非对映异构体的峰比直接确定2-氨基-1-丁醇的确切绝对光学纯度。该方法值得扩展到其他手性氨基醇的绝对光学纯度评估。

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