Generation of Hydrogen Cyanide from the Reaction of Oxyma (Ethyl Cyano(hydroxyimino)acetate) and DIC (Diisopropylcarbodiimide),Organic Process Research & Development

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Generation of Hydrogen Cyanide from the Reaction of Oxyma (Ethyl Cyano(hydroxyimino)acetate) and DIC (Diisopropylcarbodiimide)
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2019-09-04 00:00:00 , DOI: 10.1021/acs.oprd.9b00344
Adam D. McFarland ₁ , Jonas Y. Buser ₁ , Matthew C. Embry ₁ , Charles B. Held ₁ , Stanley P. Kolis ₁

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Evolution of hydrogen cyanide (HCN) during amino acid activation using the reagent combination ethyl cyano(hydroxyimino)acetate (Oxyma)/diisopropylcarbodiimide (DIC) is observed under ambient conditions (20 °C) in N,N-dimethylformamide (DMF). Concentration versus time profiles obtained by ¹H NMR spectroscopy in the presence and absence of amino acids indicate that HCN is formed upon addition of DIC to the reaction mixture and that HCN evolution continues to occur even after amino acid activation is complete when Oxyma and DIC are used in excess amounts relative to the amino acid. A mechanism for the reaction between Oxyma and DIC is proposed, and evidence for its validity was gathered by NMR spectroscopy.

中文翻译：

由氧（氰基（羟基亚氨基）乙酸乙酯）与DIC（二异丙基碳二亚胺）反应生成氰化氢

在环境条件下（20°C），在N，N-二甲基甲酰胺（DMF）中，使用氰基（羟基亚氨基）乙酸乙酯（Oxyma）/二异丙基碳二亚胺（DIC）试剂组合观察到了氨基酸活化过程中氰化氢（HCN）的释放。在存在和不存在氨基酸的情况下，通过¹ H NMR谱图获得的浓度与时间的关系曲线表明，向反应混合物中添加DIC时会形成HCN，并且即使当Oxyma和DIC均被激活后，即使氨基酸激活完成，HCN仍会继续发生。相对于氨基酸过量使用。提出了氧化酶与DIC之间反应的机理，并通过NMR光谱收集了其有效性的证据。

更新日期：2019-09-04

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