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【结 构 式】 
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【分子编号】45091 【品名】sodium 2-[(8-hydroxyoctanoyl)(methyl)amino]-1-ethanesulfonate 【CA登记号】 |
【 分 子 式 】C11H22NNaO5S 【 分 子 量 】303.355188 【元素组成】C 43.55% H 7.31% N 4.62% Na 7.58% O 26.37% S 10.57% |
合成路线1
该中间体在本合成路线中的序号：(XXII)6) The title product [14C]-labeled at C8 of the suberic acid moiety is synthesized starting from 7-bromoheptanoic acid (XVII), which is reduced with borane/dimethylsulfide complex in THF to 7-bromoheptanol (XVIII). The protection of (XVIII) with dihydropyran and p-toluenesulfonic acid affords the tetrahydropyranyl ether (XIX), which is condensed with [14C]-sodium cyanide to give 8-(tetrahydropyranyloxy)octanenitrile (XX). The hydrolysis of (XX) with 6N NaOH yields the corresponding protected acid (XXI), which is condensed with N-methyltaurine sodium salt (III) by means of carbonyldiimidazole (CDI) and deprotected in acidic medium to afford [1-14C]-8-hydroxy-N-methyl-N-(2-sulfoethyl)octanamide sodium salt (XXII). The oxidation of (XXII) with KMnO4 in water gives [8-14C]-8-oxo-8-[N-(2-sulfoethyl)-N-methylamino]octanoic acid (XXIII), which is finally condensed with methylprednisolone 21-O-mesylate (IX) in the usual way.
| 【1】 Stolle, W.T.; Runge, T.A.; Hsi, R.S.P.; Synthesis of carbon-14 and tritium labeled methylprednisolone suleptanate. J Label Compd Radiopharm 1990, 28, 255-80. |
| 【2】 Graul, A.; Leeson, J.; Castaner, J.; Methylprednisolone Suleptanate. Drugs Fut 1997, 22, 8, 833. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 11822 | 7-[N-Methyl-N-(2-sulfoethyl)carbamoyl]heptanoic acid disodium salt | C11H19NNaO6S | 详情 | 详情 | |
| (IX) | 11828 | 2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl methanesulfonate | C23H32O7S | 详情 | 详情 | |
| (XVII) | 11836 | 7-Bromoheptanoic acid | 30515-28-7 | C7H13BrO2 | 详情 | 详情 |
| (XVIII) | 11837 | 7-Bromo-1-heptanol | 10160-24-4 | C7H15BrO | 详情 | 详情 |
| (XIX) | 11838 | 1-Bromo-8-tetrahydropyranyloxyoctane; 8-Bromooctyl tetrahydro-2H-pyran-2-yl ether; 2-[(8-Bromooctyl)oxy]tetrahydro-2H-pyran | 50816-20-1 | C13H25BrO2 | 详情 | 详情 |
| (XX) | 11839 | 9-(Tetrahydro-2H-pyran-2-yloxy)nonanenitrile | C14H25NO2 | 详情 | 详情 | |
| (XX) | 45089 | 9-(tetrahydro-2H-pyran-2-yloxy)nonanenitrile | C14H25NO2 | 详情 | 详情 | |
| (XXI) | 11840 | 9-(Tetrahydro-2H-pyran-2-yloxy)nonanoic acid | C14H26O4 | 详情 | 详情 | |
| (XXI) | 45090 | 9-(tetrahydro-2H-pyran-2-yloxy)nonanoic acid | C14H26O4 | 详情 | 详情 | |
| (XXII) | 11841 | sodium 2-[(8-hydroxyoctanoyl)(methyl)amino]-1-ethanesulfonate | C11H22NNaO5S | 详情 | 详情 | |
| (XXII) | 45091 | sodium 2-[(8-hydroxyoctanoyl)(methyl)amino]-1-ethanesulfonate | C11H22NNaO5S | 详情 | 详情 | |
| (XXIII) | 11842 | sodium 2-[(7-carboxyheptanoyl)(methyl)amino]-1-ethanesulfonate | C11H20NNaO6S | 详情 | 详情 | |
| (XXIII) | 45092 | sodium 2-[(7-carboxyheptanoyl)(methyl)amino]-1-ethanesulfonate | C11H20NNaO6S | 详情 | 详情 |