グルタルイミド

解説グルタルイミド，2,6-piperidinedione．C5H7NO2(113.12)．グルタル酸イミドともいう．グルタル酸と尿素を反応させることによって得られる．"白色の結晶．融点152～154 ℃．密度1.393 g cm－3．一般に，グルタルイミド骨格を有する化合物は抗真菌，抗ウイルス活性などの薬理活性を示すので，誘導体が医薬品として用いられる．[CAS 1121-89-7]森北出版「化学辞典（第2版）

用途有機合成原料。

使用Glutarimide acts as an inhibitor of protein synthesis. Further, it is used as a reactant for thionations and biocatalytic asymmetric synthesis of sitagliptin production. It is also employed in the generation of beta-adrenoceptor ligands, enantioselective synthesis of securinega alkaloids and alfa-fluoro-alfa amino amides. In addition to this, it is used in intramolecular amidocyclopropanation reactions.

一般的な説明A glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities.

製造方法To a flask containing 70 gm (0.53 mole) of glutaric acid is added 150 ml (2.2 mole) of 28% aqueous ammonia. The mixture is set for distillation and heated for 7 hr as the temperature of the mixture rises from 90° to 180°C. The temperature is held at 170-180°C for \\ hr or until the evolution of ammonia ceases. The reaction mixture solidifies on cooling and the pro­duct is recrystallized from acetone to afford 37.4 gm (63%), m.p. 145-146°C. t may be advantageous to preform the ammonium salt of dicarboxylic acids prior to the application of enough heat to form the imide. The preparation of succinimide is a case in point.

純化方法Purify it by dissolving 75g in 200mL of H2O, boil for 30minutes with 2g of charcoal, filter, evaporate to dryness and recystallise the residue from 125mL of 95% EtOH to give 70g of white crystals, m 152-154o. It also crystallises from Me2CO (m 163-165o) or EtOH (m 153-154o). The N-bromo derivative (a brominating agent) crystallises from H2O with m 180-185o. [Paris et al. Org Synth Coll Vol IV 496 1963, Beilstein 21 H 382, 21 I 331, 21 II 307, 21 III/IV 4582.]