Synthetic Route of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: A mixture of 3,4-dihydroxycinnamic acid (497mg, 2.76mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (794mg, 4.14mmol), 1-hydroxybenzotriazole (HOBt) (559mg, 4.14mmol), Et3N (0.58mL, 4.14mmol) in anhydrous DMF (10mL) was stirred under an atmosphere of argon for 10minat 26C. Propane-1,3-diamine (102mg, 1.38mmol) was added, and the mixture was stirred for 18hat 26C. The mixture was concentrated under reduced pressure to give a crude coupling product of the title compound (2). To facilitate isolation, the coupling product was treated with Ac2O (10mL) in pyridine (10mL) at 26C for 12h. The mixture was concentrated, and extracted with EtOAc and water for three times. The organic layers were combined and washed with water (10mL) and brine (10mL). The organic phase was dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (EtOAc elution) to afford the acetylation compound. To a solution of the acetylation compound in MeOH (10mL) was added K2CO3 (13mg, 0.13mmol). The mixture was stirred for 0.5hat 26C, and then acidified to pH 5 by addition of Dowex 50WX8-200 cationic exchange resin. The resin was then removed by filtration. The filtrate was concentrated, and purified by silica gel chromatography (EtOAc, then MeOH/CH2Cl2 1:4) to give pure compound 2 (146mg, 27% yield).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.
Reference:
Article; Tu, Ling-Hsien; Tseng, Ning-Hsuan; Tsai, Ya-Ru; Lin, Tien-Wei; Lo, Yi-Wei; Charng, Jien-Lin; Hsu, Hua-Ting; Chen, Yu-Sheng; Chen, Rong-Jie; Wu, Ying-Ta; Chan, Yi-Tsu; Chen, Chang-Shi; Fang, Jim-Min; Chen, Yun-Ru; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 393 – 404;,
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