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【结 构 式】 
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【分子编号】10041 【品名】2-Methoxy-5-((2R)-2-[[(1R)-1-phenylethyl]amino]propyl)benzenesulfonamide 【CA登记号】 |
【 分 子 式 】C18H24N2O3S 【 分 子 量 】348.46624 【元素组成】C 62.04% H 6.94% N 8.04% O 13.77% S 9.2% |
合成路线1
该中间体在本合成路线中的序号：(IV)A new synthesis of YM-12617-1, the active R-isomer of YM-12617, has been described: The reductocondensation of 1-(4-methoxyphenyl)-2-propanone (I) with R-1-phenylethylamine (II) gives regioselectively the secondary amine (III) as the HCl salt, which by sulfonation with chlorosulfonic acid and treatment with NH4OH yields (R,R)-2-methoxy-5-[2-(1-phenylethylamino)propyl]benzenesulfonamide (IV). Eliminating the protecting group by hydrogenation, the free amine hydrochloride (V) is obtained, which is finally submitted to a reductocondensation with 2-(2-ethoxyphenoxy)acetaldehyde (VI) by means of sodium borohydride in methanol, and treated with HCl in ether.
| 【1】 Hunden, D.C.; Wheller, W.J.; Schmiegel, K.K.; The synthesis of the 14C and 2H-isotopomers of (R)-N-[2-(2'-ethoxyphenoxy)-ethyl]-N-2-[3-(4'-methoxy-3'-sulfonamido)-phenyl]-propylamine hydrochloride, an alpha1-adrenoreceptor antagonist. J Label Compd Radiopharm 1989, 26, 2, 171. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 10038 | 4-Methoxyphenylacetone; 1-(4-Methoxyphenyl)acetone | 122-84-9 | C10H12O2 | 详情 | 详情 |
| (II) | 10039 | (1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine | 3886-69-9 | C8H11N | 详情 | 详情 |
| (III) | 10040 | (2R)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]-2-propanamine; N-[(1R)-2-(4-Methoxyphenyl)-1-methylethyl]-N-[(1R)-1-phenylethyl]amine | C18H23NO | 详情 | 详情 | |
| (IV) | 10041 | 2-Methoxy-5-((2R)-2-[[(1R)-1-phenylethyl]amino]propyl)benzenesulfonamide | C18H24N2O3S | 详情 | 详情 | |
| (V) | 10042 | 5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide | 112101-81-2 | C10H16N2O3S | 详情 | 详情 |
| (VI) | 10043 | 2-(2-Ethoxyphenoxy)acetaldehyde | 103181-55-1 | C10H12O3 | 详情 | 详情 |