酰胺(Amide)

• 贡献者：彭玉婷；整理：陈宇暄

脱水制丁腈(Dehydration to Nitrile)

A variety of dehydrating agents can be used, including P2O5, TCCA, and tosyl chloride.

可使用多种脱水剂，包括五氧化二磷、TCCA和托氯。

To a solution of the amide (1.15 g, 3.6 mmol) and para-toluenesulfonyl chloride (1.91 g, 7.2 mmol) in CH2Cl2 (9 mL) was added pyridine (1.46 mL, 18 mmol). After complete reaction, as judged by TLC, saturated aqueous NaHCO3 was carefully added. The resultant two-phase mixture was stirred vigorously for 2 h before the layers were separated and the organic phase was washed with 1 M aqueous HCl and then another portion of saturated aqueous NaHCO3. The aqueous phases were back extracted with CH2Cl2 and the combined organic phases were dried, filtered, and concentrated to leave a crude product. This crude product was purified by column chromatography to provide the nitrile (1.02g, 94%).

在二氯甲烷（9 mL）中的酰胺（1.1.15g，3.6 mmol）和对甲苯磺酰氯（1.91 g，7.2 mmol）溶液中加入吡啶（1.46 mL，18 mmol）。反应完成后，通过薄层色谱法判断，仔细加入饱和的碳酸氢钠水溶液。将合成的两相混合物大力搅拌2小时，然后分离各层，然后用1M盐酸水溶液和另一部分饱和碳酸氢钠水溶液洗涤有机相。水相用二氯甲烷反提，组合有机相干燥、过滤，浓缩留下粗产物。该粗产物经柱层析纯化，得到丁腈（1.02g，94%）。

Reference: McLaughlin, M.; Mohareb, R. M.; Rapoport, H. J. Org. Chem. 2003, 68, 50–54.

参考文献: McLaughlin, M.; Mohareb, R. M.Rapoport,H.J.Org.Chem.2003,68,50–54.

水解成酸(Hydrolysis to Acid)

Amides are much more robust than esters but can be hydrolyzed under vigorous conditions.

酰胺比酯更坚固，但在强烈的条件下可以水解。

R-(+)-2-Methyl-2-hydroxy-3-phenylpropionamide (179 mg, 1 mmol) was refluxed in hydrochloric acid (6 N, 29 ml) for 3 h to give, after extraction with EtOAc and column chromatography using a silica gel column with a mixture of petroleum ether and EtOAc (1:2) as an eluent, R-(+)-2-methyl-2-hydroxy-3-phenylpropionic acid as a white solid (166 mg, 92%).

R-(+)-2-甲基-2-羟基-3-苯基丙酰胺（179mg，1 mmol）在盐酸(6 N，29ml）中回流3小时，用乙酸乙酯提取和柱层析使用硅胶柱以石油醚和乙酸乙酯（1：2）作为洗脱液，R-(+)-2-+-2-甲基-羟基-3-苯基丙酸作为白色固体（166mg，92%）。

参考文献: Wang, M.-X.; Deng, G.; Wang, D.-X.; Zheng Q.-Y. J. Org. Chem. 2005, 70, 2439–2444.