3,5-二取代手性海因的合成

Synthesis of 3,5-Disubstituted Chiral Hydantoin

研究了以混合溶剂法由氨基酸和异氰酸苯酯合成 3 ,5 二取代手性海因的工艺 ,合成的 4种手性海因 ( 5R) 5 ( 5 咪唑甲基 ) 3 苯基 2 ,4 咪唑啉二酮、( 5R) 5 苄基 3 苯基 2 ,4 咪唑啉二酮、( 5S) 5 甲基 3 苯基 2 ,4 咪唑啉二酮和 ( 5S) 5 羟甲基 3 苯基 2 ,4 咪唑啉二酮均具有一定的光学活性 ,经元素分析、IR及1HNMR分析证实其结构与预期结构完全一致。详细探讨了原料配比、溶液pH值、反应温度等对手性海因制备结果的影响。实验表明 ,本工艺操作简便 ,最高产率达75 %。

Synthesis of 3,5-disubstituted chiral hydantoin with amino acid and phenyl isocyanate in mixed solvent was studied. Thus, four kinds of hydantoins, (5R)-5-(5-imidazolylmethyl)-3-phenyl-2,4-imidazolidinedione, (5R)-5-benzyl-3-phenyl-2,4-imidazolidinedione,(5S)-5-methyl-3-phenyl- 2, 4-imidazolidinedione and (5S)-5-hydroxymethyl-3-phenyl-2,4-imidazolidinedione, were prepared, which all have certain optical activity and were proved to have the expected structures by elementary analysis, IR and 1HNMR spectroscopy. Effects of ratio of raw materials, pH value of reaction mixture and reaction temperature on the preparation of chiral hydantoins were discussed. Result of the experiment showed that the process is easy to operate with the highest yield of 75%.