Method for synthesizing 4-substituted oxazolidinone derivatives simply and efficiently

一种简单、高效合成4-取代噁唑烷酮衍生物的方法

Abstract

The invention relates to a method for synthesizing 4-substituted oxazolidinone simply and efficiently. The method comprises the following steps of: protecting amino in diethyl ether, wherein alpha-substituted amino-acid ester serves as a raw material; adding the protective group-containing amino-acid ester into tetrahydrofuran at room temperature; adding sodium borohydride slowly into the mixture to perform a reduction reaction; and after the reaction is finished, neutralizing and extracting so as to obtain the 4-substituted oxazolidinone simply and efficiently. The reaction has only one step, so that the process is simple without cocatalyst alkali; the raw material has low price and is a readily available chemical product; the using amount of the catalyst sodium borohydride is small and the catalytic effect is good; and an organic solvent used in the reaction is easy to recycle, so that the whole reaction process is a clean and high-efficiency process and large-scale industrialized production is facilitated. A single antipode is obtained without racemization of a chiral substrate and products in the reaction process and the aftertreatment process.
一种简单、高效合成4-取代噁唑烷酮的方法。用α-取代氨基酸酯为原料,在乙醚中对氨基进行保护后,在室温条件下,将带保护基的氨基酸酯加入四氢呋喃中,慢慢加入硼氢化钠对其进行还原。反应结束后,经中和、萃取,即可简便、高收率地得到4-取代噁唑烷酮。反应步骤仅有一步,过程简单,不使用助催化剂碱;原料价廉,是一种容易得到的化工产品;催化剂硼氢化钠的用量少,催化效果好;反应使用的有机溶剂易回收并循环利用,使得整个反应过程成为清洁、高效的工艺流程,有利于大规模工业化生产。对于手性底物,反应过程及后处理过程产物都不发生消旋而得到单一的对映体。

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Patent Citations (2)

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NO-Patent Citations (1)

    Title
    《J.Org.Chem.》 20051021 Jason E.Hein et al. Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliariesfrom r-Amino Acids 9940-9946 1-8 第70卷, 第24期 2

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