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【结 构 式】

【分子编号】65229

【品名】 

【CA登记号】 

【 分 子 式 】C28H54.2[Cr(CO)3]

【 分 子 量 】526.965648

【元素组成】C 70.66% H 10.37% Cr 9.87% O 9.11%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXXI)

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.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IIIa) 18697 1,4-bis(bromomethyl)benzene 623-24-5 C8H8Br2 详情 详情
(I) 25362 1,4,8,11-Tetraazacyclotetradecane 295-37-4 C10H24N4 详情 详情
(XXX) 65228     C10H24.Cr(CO)3 详情 详情
(XXXI) 65229     C28H54.2[Cr(CO)3] 详情 详情
(XXXII) 65230     C10H21N4OP 详情 详情
(XXXIII) 65231     C28H48N8O2P2 详情 详情
Extended Information