FACILE TRANSFORMATION OF ANTIVIRAL THIOAMIDES INTO AMIDES

已知硫代酰胺的氧化脱硫是在体内发生的。为 硫代酰胺的代谢研究，需要相应的酰胺作为 一种参考材料使我们的注意力集中在化学转化上。 由硫代酰胺制备酰胺的合成方法有多种 不足之处。在验证某些结构的研究中 抗病毒硫代酰胺，电子电离质谱图 下定决心。一种常见的碎裂，从分子中损失了33amu 观察到自由基阳离子。精确的质量测量表明，这是 碎裂与SH自由基的丧失相对应。轻而易举地失去了 Shh让我们注意寻找一种合适的试剂，这种试剂可以 起氧交换剂的作用。我们发现甲基亚砜可以 表现得像这样的代理人。因此，硫代酰胺是快速和定量的 转化为相应的酰胺类化合物 常温下甲基亚砜中的盐酸。 量化转换迅速实现，通常不到一次 在室温下保持分钟，不对反应进行进一步处理 仪器分析需要混合液。确凿的证明 起始硫代酰胺和产品酰胺部分的完整性为 通过气相傅里叶变换红外光谱分析得到。

Oxidative desulfurization of thioamides is known to occur in vivo. For metabolic studies of thioamides, the need for the corresponding amide as a reference material focussed our attention on the chemical conversion. Synthetic methods for preparation of amides from thioamides have numerous deficiencies. During studies to verify the structures of certain antiviral thioamides, the electron-ionization mass spectra were determined. A common fragmentation, loss of 33 amu from the molecular radical cation, was observed. Exact mass measurements showed that this fragmentation corresponds to the loss of SH radical. The facile loss of SH directed our attention to a search for a suitable reagent which could function as an oxygen-exchange agent. We have found methyl sulfoxide to behave as such an agent. Thus, thioamides are quickly and quantitatively transformed into their corresponding amides by treatment with hydrochloric acid in methyl sulfoxide at ambient temperature. Quantitative conversion is rapidly achieved, typically in less than one minute, at room temperature and no further processing of the reaction mixture is required for instrumental analysis. Unequivocal proof of the integrity of the starting thioamide and the product amide moieties was obtained by gas phase Fourier-transformed infrared spectroscopy.