杏耀国际

氰基乙酸乙酯肼解得到的氰基乙酰肼经过亚硝酸处理得到氨基酸的反应。

反应机理

亚硝酸处理酰肼得到酰基叠氮，接着进行Curtius重排，水解得到氨基酸。

反应实例

DL-β-Methylleucine (5). To stirred cyano hydrazide 4 (50 mmol) in 100 mL 15% HCl at 0 C was added 75 mL ether followed dropwise by 10 g of NaNO2 in 30 mL H2O. The ether layer and ether extract of the aq layer were added to 75 mL of abs EtOH. Ether was evaporated. The mixture was refluxed for 1h and after EtOH was distilled, it was refluxed in 200 mL of 20% HCl at 140 C for

2 days. After evaporation, the residue in water was boiled with charcoal, neutralized and treated with 2.5 L Me2CO to give 5 (50%), mp 168 C.

【Gagnon PE, Can J Chem., 1951, 29, 70】

相关文献

1 Darapski J Prakt Chem 1915 92 297

2 Gagnon PE Can J Chem 1951 29 70

3 Crami A J Org Chem 1960 25 44

编译自：Organic Syntheses Based On , 3RdEd, A. Hassner, Page 114.

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