The effect of the change of 5,6-Diamino-1,10-phenanthroline synthetic route on the product

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The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular.55750-49-7, name is Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate. A new synthetic method of this compound is introduced below., 55750-49-7

55750-49-7, A solution of 82 (278 mg, 0.55 minol) in Tesser?s Base (20 mL, i,4-dioxane/methanol/4M NaOH, 30:9:1 v/v) was stirred at room temperature for 10 minutes. The solution was then concentrated in vacuo to afford a yellow oil, which was used without further purification. To the crude oil was added a mixture of 45 (163 mg, 0.66 minol) in saturated aqueous sodium bicarbonate (14 mL), and the mixture stirred at room temperature for 5 minutes. Themixture 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 83 (100 mg, 50%) as a yellow oil. [aID232 = -1.0 (c 1.00 in CHCI3); 1H NMR (400 MHz, CDCI3) oe 1.33-1.41 (2H, m, H-3?), 1.44 (9H, s, Boc), 1.59-1.69 (2H, m, H-4?), 1.81-1.95(2H, m, H-2?), 2.39 (3H, s, 3?-Me), 3.51 (2H, t, J = 7.2 Hz, H-5?), 4.97-5.01 (iH, m, H-i?),5.09 (iH, d, J = 7.4 Hz, NH), 6.69 (2H, 5, H-3, H-4); 13C NMR (100 MHz, CDCI3) oe 11.5 (CH3, 3?-Me), 22.4 (CH2, C-3?), 27.9 (CH2, C-4?), 28.3 (3 x CH3, Boc), 33.4 (CH2, C-2?),37.2 (CH2, C-5?), 48.0 (CH, C-i?), 80.4 (C, Boc), 134.1 (2 x CH, C-3, C-4), i55.0 (C, Boc),i67.i (C, C-3?), i70.8 (2 x C, C-2, C-5), 179.1 (C, C-5?); Vmax (cm1) 3336, 2925, i702,1514, i367, ii64, 828; HRMS-ESI [M+Na] Calcd. for C17H24N4O5Na 387.i639, found387. i652.

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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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