Bouveault-Locquin氨基酸合成反应

丙二酸酯经过亚硝酸化-脱羧得到α-酮肟酯，接着还原生成氨基酸的反应。

反应机理

反应操作

Ethyl a-(hydroxyimino)-b-phenylpropanoate (3). Malonate 1 (50 g, 0.2 mol) in EtOH (92 mL) was treated with EtONa (13.6 g, 0.2 mol) and ethyl nitrite 2 (22.5 g, 0.3 mol) at 0 C. The mixture was kept at r.t. for 20 h. After solvent evaporation at r.t. under vacuum, cold conc HCl was added to pH 5. Extraction (Et2O) and evaporation gave 40 g of 3 (97%), mp 54–57 C.

Ethyl phenylalaninate (4). 3 (16.8 g, 80 mmol) in EtOH(850 mL) and Raney nickel was hydrogenated at 70–75 C. Filtration of catalyst and evaporation gave 8.3 g of 4 (53%), bp 141–142 C (10 mm).

【Hauser CR, J Am Chem Soc, 1947, 69, 1264】

相关文献

1 Bouveault L, Locquin R Compt Rendu 1902 135 179

2 Hauser CR J Am Chem Soc 1947 69 1264

3 Li HY J Org Chem 2001 66 4148

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 57.