沈家祥, 谢侃, 蔡一忠, 田化宇, 高怡生, 陆顺兴, 陈润莲. 氯霉素之合成研究(五) DL-threo-1-对硝基苯-2-氨基-1,3-丙二醇的分拆J. 药学学报, 1958, 6(4): 219-227.
引用本文: 沈家祥, 谢侃, 蔡一忠, 田化宇, 高怡生, 陆顺兴, 陈润莲. 氯霉素之合成研究(五) DL-threo-1-对硝基苯-2-氨基-1,3-丙二醇的分拆J. 药学学报, 1958, 6(4): 219-227.
SHEN CHIA-CHIANG SIE KAN TSAI J-ZHONG TIEN HUA-YU KAO YEE-SHENG LOH SHUEN-HSING CHEN RYN-LIAN, . STUDIES RELATED TO THE SYNTHESIS OF CHLORAMPHENICOL.Ⅴ RESOLUTION OF DL-THREO-1-p-NITROPHENYL-2-AMINO-1,3-PROPANEDIOLJ. Acta Pharmaceutica Sinica, 1958, 6(4): 219-227.
Citation: SHEN CHIA-CHIANG SIE KAN TSAI J-ZHONG TIEN HUA-YU KAO YEE-SHENG LOH SHUEN-HSING CHEN RYN-LIAN, . STUDIES RELATED TO THE SYNTHESIS OF CHLORAMPHENICOL.Ⅴ RESOLUTION OF DL-THREO-1-p-NITROPHENYL-2-AMINO-1,3-PROPANEDIOLJ. Acta Pharmaceutica Sinica, 1958, 6(4): 219-227.

氯霉素之合成研究(五) DL-threo-1-对硝基苯-2-氨基-1,3-丙二醇的分拆

STUDIES RELATED TO THE SYNTHESIS OF CHLORAMPHENICOL.Ⅴ RESOLUTION OF DL-THREO-1-p-NITROPHENYL-2-AMINO-1,3-PROPANEDIOL

  • 摘要: 研究了应用酒石酸来分拆DL-threo-1-对-硝基苯-2-氨基-1,3-丙-二醇为旋光体的基本数据。首先制备了D-和L-threo-1-对硝基苯-2-氨基-1,3-丙二醇,它們底酸性酒石酸盐和正酒石酸鹽,测定了物理常數(表1)。D-和L-threo-1-对-硝基苯-2-氨基-1,3-丙二醇的混合熔点曲線提示了混旋化合物的存在(圖1)。事实上,DL-化合物和其各別旋光体在水中的溶解度也不同(圖2). 酸性酒石酸盐和正酒石酸鹽在甲醇中,以及前者在水中的溶解度曲線,均經分別测定(圖3—5)。据此,我們建議了通过酸性酒石酸鹽,以甲醇或水为溶剂来提取的,旋光体分拆方法。

     

    Abstract: Basic data useful for the resolution of DL-threo-1-p-nitrophenyl-2-amino-1, 3-propanediol with tartaric acid were studied. Pure samples of D- and L-threo-1-p-nitrophenyl-2-amino-1, 3-propanediol, their bitartrates and normal tartrates were prepared and their physical constants determined (Table 1). Mixed melting point curve of D- and L-threo-1-p-nitro-phenyl-2-amino-1, 3-propanediol (Fig. 1) indicated the presence of a racemic compound as evidenced by a shortening of the melting range at 1:1 composition. Indeed, solubilities of the DL- compound and its optically active components in water also differred (Fig. 2). Solubility curves of the different bitartrates and normal tartrates in methanol and the bitartrates in water were shown in Fig. 3 to Fig. 5 respectively. Based upon these data, procedures for resolution through the bitartrates were suggested, using either water or methanol as solvent. However, as a consequence of greater solubility, the procedure using water as solvent called for an extraction temperature of only 15℃ above that of room temperature, and the mother liquor should be recycled after being cooled to separate the L-threo-1-p-nitrophenyl-2-amino-1, 3-propanediol bitartrate.

     

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