With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.137076-54-1,2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid,as a common compound, the synthetic route is as follows.
Example 4- Synthesis of tri-tert-butyl 2,2′,2′-(10-(2-((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate To a solution of product 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid (572.7 mg, 1 mmol) in dry DMF (15 mL), amino-maleimide 137 (483.3 mg, 1 mmol) was added with HATU (272 mg, 1.4 mmol) and DIPEA (360 muL, 1.84 mmol). The mixture was stirred overnight at room temperature. After removing the solvent under the vacuum, the crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 90:10) to give compound tri-tert-butyl 2,2′,2′-(10-(2-((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate as a white foam (396 mg, 57 %). Rf : 0.3 (CH2Cl2/MeOH, 90:10). 1H NMR (300MHz, CDCl3) delta 8.30 (b, 1H, NH), 6.86 (s,2H, H6′), 3.78-3.54 (br, 4H, H3′, H4′), 3.54 (br, 4H, H13, H1′), 3.48 (br, 4H, H8), 3.09-2.99 (m, 8H, H2, H3), 2.97-2.86 (m, 8H, H5, H6), 1.46 (s, 18H, H12), 1.45 (s, 9H, H17). 13C NMR (75MHz, CDCl3) delta 171.6 (C2′), 171.0 (C5′), 170.4 (C9, C14), 134.2 (C6′), 81.5 (C16), 81.3 (C11), 57.8 (C1′), 55.7-55.2 (C8, C13), 54.1-51.5 (C2, C3), 51.0-48.9 (C5, C6), 38.0 (C4′), 32.7 (C3′), 27.8 (C17), 27.6 (C12). MS (ESI) : m/z 695 [M + H]+.
137076-54-1, 137076-54-1 2-(4,7,10-Tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid 11606627, acatalyst-ligand compound, is more and more widely used in various fields.
Reference£º
Patent; Institut Curie; Centre National de la Recherche Scientifique; The designation of the inventor has not yet been filed; EP2740491; (2014); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI