M Baldwin Oliver W, Conrad-Marut Linden H, Beutner Gregory L, Vosburg David A
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, California 91711, United States.
Chemical and Synthetic Development, Bristol Myers Squibb, One Squibb Drive, New Brunswick, New Jersey 08903, United States.
J Chem Educ. 2022 Nov 8;99(11):3747-3751. doi: 10.1021/acs.jchemed.2c00760. Epub 2022 Oct 3.
A new undergraduate organic laboratory experiment has been developed for amide bond formation between biorenewable 2-furoic acid and either of two substituted piperazines to prepare medicinally relevant amide products using a procedure with industrial significance. The reactions proceeded smoothly under ambient conditions using the combination of -tetramethylchloroformamidinium hexafluorophosphate (TCFH) and -methylimidazole (NMI) in a minimal volume of acetonitrile with a direct crystallization upon addition of water. Students successfully collected their product by filtration and then characterized it by NMR (H, C, COSY, DEPT-135, HSQC), IR, MS, and melting point. Students also explored the reaction mechanism and compared green chemistry aspects of their procedure with literature routes. A virtual version of the experiment was adapted for remote instruction.
已开发出一种新的本科有机实验室实验，用于在生物可再生的2-呋喃甲酸与两种取代哌嗪中的任一种之间形成酰胺键，以使用具有工业意义的程序制备与药物相关的酰胺产物。在环境条件下，使用六氟磷酸四甲基氯甲脒（TCFH）和N-甲基咪唑（NMI）的组合，在最小体积的乙腈中进行反应，并在加水后直接结晶。学生们通过过滤成功收集了他们的产物，然后通过NMR（氢谱、碳谱、COSY、DEPT-135、HSQC）、红外光谱、质谱和熔点对其进行了表征。学生们还探索了反应机理，并将他们的实验步骤的绿色化学方面与文献路线进行了比较。该实验的虚拟版本适用于远程教学。
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