With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55750-49-7,Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.
55750-49-7, A solution of 62 (2.12 g, 5.4 minol), acetic acid (1.5 mL) and palladium-on-carbon (0.2 g,10% w/w) in methanol (30 mL) was stirred at room temperature under a hydrogenatmosphere for 90 minutes. The mixture was then filtered through Celite and the solution concentrated in vacuo to afford a yellow oil, which was used without further purification. To the crude oil was added a mixture of 45 (1.36 g, 8.1 minol) in saturated aqueous sodium bicarbonate (50 mL) at 0 C, and the mixture stirred at 0 C for 10 minutes. Acetonitrile (25mL) was then added and the mixture stirred at room temperature for 90 min. The mixture was then extracted with dichloromethane (3 x), the combined organic layers dried over anhydrous magnesium sulfate, filtered and the solution concentrated in vacuo. Purification by column chromatography (EtOAc/hexanes, 1:2) afforded the title compound 63 (1.43 g, 78%) as a yellow oil. [aID237 = + 11.1 (c 1.00 in CHCI3); 1H NMR (400 MHz, CDCI3) oe 1.31-1.38 (2H, m, H-4?), 1.44 (9H, s, Boc), 1.59-1.67 (3H, m, Hb-3?, H-5?), 1.79-1.83 (1H, m,Ha3?), 3.51 (2H, t, J = 7.2 Hz, H-6?), 3.74 (3H, s, OMe), 4.27 (1H, m, H-2?), 5.08 (1H, d, J= 7.9 Hz, NH), 6.70 (2H, s, H-3, H-4); 13C NMR (100 MHz, CDCI3) oe 22.4 (CH2, C-4?), 28.0(CH2, C-5?), 28.3 (3 x CH3, Boc), 32.1 (CH2, C-3?), 37.3 (CH, C-6?), 52.2 (CH3, OMe), 53.2(CH, C-2?), 79.8 (C, Boc), 134.1 (2 x CH, C-3, C-4), 155.3 (C, Boc), 170.7 (2 x C, C-2, C-5), 173.1 (C, C-i?); vmax (cm1) 3374, 2952, 1698, 1365, 1160, 828, 694; HRMS-ESI[M+Na] Calcd. for C16H24N2O6Na 363.1527, found 363.1528.
As the paragraph descriping shows that 55750-49-7 is playing an increasingly important role.
Reference£º
Patent; SAMMUT, Ivan Andrew; HARRISON, Joanne Clare; HEWITT, Russell James; READ, Morgayn Iona; STANLEY, Nathan John; WOODS, Laura Molly; KUEH, Jui Thiang Brian; JAY-SMITH, Morgan; SMITH, Robin Andrew James; GILES, Gregory; LARSEN, Lesley; RENNISON, David; BRIMBLE, Margaret Anne; LARSEN, David Samuel; (209 pag.)WO2017/95237; (2017); A1;,
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