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【结 构 式】 
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【分子编号】65231 【品名】 【CA登记号】 |
【 分 子 式 】C28H48N8O2P2 【 分 子 量 】590.689364 【元素组成】C 56.93% H 8.19% N 18.97% O 5.42% P 10.49% |
合成路线1
该中间体在本合成路线中的序号：(XXXIII)The tetraazacyclotetradecane (I) is protected as the chromium tridentate complex (XXX) upon heating with chromium hexacarbonyl in deaerated dibutyl ether. Subsequent condensation of the cyclam-Cr(CO)3 complex (XXX) with p-dibromoxylene (IIIa) produces the chromium-protected bis-cyclam (XXXI), which is deprotected to plerixafor by oxidation with air in aqueous HCl (12, 13). Alternatively, protection of (I) as the phosphorotriamide (XXXII) can be accomplished by reaction with tris(dimethylamino)phosphine, followed by oxidation with CCl4 and NaOH (12) or by treatment with POCl3 and Et3N (14). After condensation of (XXXII) with dibromide (IIIa), the dimeric bis-phosphoramide obtained (XXXIII) is hydrolyzed to the title compound by treatment with diluted HCl (12, 14). Scheme 4.
| 【12】 Handel, H., Yaouanc, J.-J., Zegzouti, A.F. et al. (Centre National de la Recherche Scientifique [CNRS]). Process for the preparation of monofunctionalized cyclic tetramines. US 5047527. |
| 【13】 Yaouanc, J.-J., Le Bris, N., Le Gall, G., Clément, J.-C., Handel, H., des Abbayes, H. Mono N-functionalization of cyclic and linear tetraamines via their tridentate tricarbonylchromium complexes. J Chem Soc Chem Commun 1991, 206-7. |
| 【14】 Guillaume, D., Marshall, G.R. Efficient one-pot synthesis of JM3100. Synth Commun 1998, 28(15): 2903-6. |