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【结 构 式】 
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【分子编号】43909 【品名】N-[(2S)-2,5-dimethyl-2-phenyl-4-hexenyl]-N-methylbenzenesulfonamide 【CA登记号】 |
【 分 子 式 】C21H27NO2S 【 分 子 量 】357.51692 【元素组成】C 70.55% H 7.61% N 3.92% O 8.95% S 8.97% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Reductive amination of 2,5-dimethyl-2-phenylhex-4-enal (X) with methylamine and NaBH3 gives the expected secondary amine as a racemic mixture that is separated by means of mandelic acid, yielding the desired isomer (XI). The sulfonylation of the resulting amine (XI) with benzenesulfonyl chloride (XII) provided sulfonamide (XIII). Dihydroxylation with N-methylmorpholine-N-oxide in the presence of a catalytic amount of osmium tetroxide gave rise to diol (XIV), which was oxidatively cleaved to aldehyde (XV) by means of sodium periodate. Finally, reductive condensation between aldehyde (XV) and piperidine (VI) furnished the title compound.
| 【1】 Chen, P.; Dorn, C.P. Jr.; Caldwell, C.G.; et al.; Synthesis and evaluation of CCR5 antagonists having potent in vitro antiviral activity. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 85. |
| 【2】 Finke, P.E.; Mills, S.G.; Caldwell, C.G.; MacCoss, M.; Wang, L.; Kothandaraman, S.; Kim, D.; Oates, B. (Merck & Co., Inc.); Cyclic amine modulators of chemokine receptor activity. EP 1052992; US 6140349; WO 9938514 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 43905 | 4-nitrobenzyl allyl(4-piperidinyl)carbamate | C16H21N3O4 | 详情 | 详情 | |
| (X) | 43906 | tert-butyl 4-([[(4-nitrobenzyl)oxy]carbonyl]amino)-1-piperidinecarboxylate | C18H25N3O6 | 详情 | 详情 | |
| (XI) | 43907 | 2,5-dimethyl-2-phenyl-4-hexenal | C14H18O | 详情 | 详情 | |
| (XII) | 14713 | benzenesulfonyl chloride | 98-09-9 | C6H5ClO2S | 详情 | 详情 |
| (XIII) | 43908 | (2S)-N,2,5-trimethyl-2-phenyl-4-hexen-1-amine; N-[(2S)-2,5-dimethyl-2-phenyl-4-hexenyl]-N-methylamine | C15H23N | 详情 | 详情 | |
| (XIV) | 43909 | N-[(2S)-2,5-dimethyl-2-phenyl-4-hexenyl]-N-methylbenzenesulfonamide | C21H27NO2S | 详情 | 详情 | |
| (XV) | 43910 | N-[(2S)-4,5-dihydroxy-2,5-dimethyl-2-phenylhexyl]-N-methylbenzenesulfonamide | C21H29NO4S | 详情 | 详情 |