Chiral Discrimination at the Solid State of Methyl 2-(Diphenylmethylsulfinyl)acetate
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- 作者：Ludovic Renou ; Thomas Morelli ; Servane Coste ; Marie-Noë ; lle Petit ; Benjamin Berton ; Jean-Jacques Malandain ; Gerard Coquerel
- 刊名：Crystal Growth & Design
- 出版年：2007
- 出版时间：September 2007
- 年：2007
- 卷：7
- 期：9
- 页码：1599 - 1607
- 全文大小：931K
- 年卷期：v.7,no.9(September 2007)
- ISSN：1528-7505
文摘
The present paper reports a study on the chiral discrimination at the solid state of methyl 2-(diphenylmethylsulfinyl)acetate (hereafter, DMSAM) as a key intermediate in the synthesis of an acetamide derivative (modafinil). A partial solid solution(i.e., stable "racemic conglomerate" with partial miscibility at the solid state) between enantiomers was characterized by X-raysingle crystal analyses and high performance liquid chromatography (HPLC). Binary and ternary phase diagrams of DMSAM wereinvestigated by HPLC measurements, differential scanning calorimetry (DSC), discontinuous isoperibolic thermal analysis (DITA),and Raman spectroscopy. Finally, the distribution of the two enantiomers inside single crystals was studied by dissolution andRaman microspectroscopy.