文献类型：期刊文献

英文题名：Diastereomeric resolution of 3-chloromandelic acid with threo-(1S,2S)-2-amino-l-p-nitrophenyl-1,3-propanediol

作者：Wang, Jie[1];Ao, Qiong[1];Peng, Yangfeng[1];Feng, Cai[2]

机构：[1]East China Univ Sci & Technol, Sch Chem Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China;[2]Shanghai Hequan Med Res & Dev Co Ltd, Preparat Business Dept, Shanghai, Peoples R China

年份：2021

卷号：33

期号：11

起止页码：824

外文期刊名：CHIRALITY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000694645500001)】；

语种：英文

外文关键词：3-chloromandelic acid; crystal packing; diastereomeric salt formation; hydrogen-bonding wall; resolution; threo-(1S; 2S)-2-amino-l-p-nitrophenyl-1; 3-propanediol

摘要：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/pi 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 center dot(R,R)-SA and (R)-4-ClMA center dot(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)-alpha-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 center dot(S,S)-SA, (R)-3-ClMA center dot(R)-PEA and (R)-3-ClMA center dot(R)-BPA were compared and examined.