An optical resolution of 3-chloromandelic acid (3-ClMA) using threo-(1S,2S)-2-amino-l-p-nitrophenyl-1,3-propanediol ([S,S]-SA) as a resolving agent was presented. The effects of the type of solvents, the amount of solvent, molar ratio of the resolving agent to racemate and filtration temperature on resolution were investigated. Under the optimal resolution conditions, the content of less soluble salt reached 98%, and the resolution efficiency was as high as 94%. The weak intermolecular interactions (such as hydrogen bond, halogen bond, CH/π and van der Waals interactions) and molecular packing mode in crystal structure of the less soluble salt (R)-3-ClMA(S,S)-SA were investigated. A wall-like 2-D hydrogen-bonding network and hydrophobic structure between hydrogen-bonding walls were revealed. (S,S)-SA was also used to resolve 2-ClMA and 4-ClMA respectively and the corresponding less soluble salts (R)-2-ClMA·(R,R)-SA and (R)-4-ClMA·(R,R)-SA were obtained using threo-(1R,2R)-2-amino-l-p-nitrophenyl-1,3-propanediol ((R,R)-SA) as a resolving agent. In addition, two other resolving agents, (R)-ɑ-phenethylamine ((R)-PEA) and (R)-N-benzyl phenethylamine ((R)-BPA) reported in the literature for the resolution of 3-ClMA were examined along with the newly proposed resolving agent, (S,S)-SA. The crystal structures of the resulting less soluble salts (R)-3-ClMA·(S,S)-SA, (R)-3-ClMA·(R)-PEA and (R)-3-ClMA·(R)-BPA were compared and examined.

中文翻译：

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使用 threo-(1S,2S)-2-amino-lp-nitrophenyl-1,3-propanediol 对 3-氯扁桃酸进行非对映体拆分

使用 threo-(1 S ,2 S )-2 -amino - l - p -nitrophenyl-1,3-propanediol ([ S , S ]-SA) 作为3-氯扁桃酸 (3-ClMA) 的光学拆分提出了解决剂。考察了溶剂种类、溶剂用量、拆分剂与外消旋体的摩尔比和过滤温度对拆分的影响。在最佳拆分条件下，难溶盐含量达到98%，拆分效率高达94%。难溶性盐( R )-3-ClMA( R )-3-ClMA(S , S )-SA 进行了研究。揭示了壁状二维氢键网络和氢键壁之间的疏水结构。( S , S )-SA 还分别用于分离 2-ClMA 和 4-ClMA 以及相应的难溶盐 ( R )-2-ClMA·( R , R )-SA 和 ( R )-4-ClMA· （- [R ，- [R使用苏- （1获得）-SA - [R，2 - [R）-2-氨基升- p硝基苯基-1,3-丙二醇（（[R ，- [R）-SA）作为拆分试剂。此外，另外两种解析剂，（R )-ɑ-苯乙胺 (( R )-PEA) 和 ( R )- N-苄基苯乙胺 (( R )-BPA) 在文献中报道的用于拆分 3-ClMA 与新提出的拆分剂一起进行了检查， ( S , S )-SA。所得难溶性盐 ( R )-3-ClMA·( S , S )-SA, ( R )-3-ClMA·( R )-PEA 和 ( R )-3-ClMA·( R )的晶体结构-BPA 进行了比较和检查。