FACILE TRANSFORMATION OF ANTIVIRAL THIOAMIDES INTO AMIDES

已知硫代酰胺的氧化脱硫在体内发生。 为 硫代酰胺的代谢研究，需要相应的酰胺作为 一份参考材料使我们的注意力集中在化学转化上。 用于从硫代酰胺制备酰胺的合成方法具有许多 缺陷 在验证某些化合物结构的研究中， 抗病毒硫代酰胺，电子电离质谱， 测定 一种常见的片段化，从分子中丢失33 amu， 自由基阳离子，观察。 精确的质量测量表明， 断裂对应于SH自由基的损失。 轻易失去 SH将我们的注意力转向寻找一种合适的试剂， 作为氧交换剂。 我们发现甲基亚砜 做这样的代理人。 因此，硫代酰胺快速且定量地 通过用以下物质处理而转化成其相应的酰胺 盐酸在甲基亚砜中在环境温度下。 定量转化是快速实现的，通常在不到一个 分钟，在室温下，并且不进一步处理反应 仪器分析需要混合物。 明确的证据 起始硫代酰胺和产物酰胺部分的完整性 通过气相傅里叶变换红外光谱法获得。

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.