|
【结 构 式】 
|
【分子编号】38783 【品名】N-([(5S)-3-[3-fluoro-4-(1-oxohexahydro-1lambda(4)-thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide 【CA登记号】 |
【 分 子 式 】C17H21FN2O4S 【 分 子 量 】368.4292232 【元素组成】C 55.42% H 5.75% F 5.16% N 7.6% O 17.37% S 8.7% |
合成路线1
该中间体在本合成路线中的序号：(II)The known dihydrothiopyran derivative (I) was hydrogenated over PtO2 to produce a mixture of cis tetrahydrothiopyran sulfoxide (II) and sulfide (III), which were separated by column chromatography. Oxidation of sulfide (III) using m-chloroperbenzoic acid then yielded a mixture of cis and trans sulfoxides, from which the title trans isomer was isolated by preparative HPLC.
| 【1】 Martin, J.P. Jr.; Barbachyn, M.R.; Poel, T.-J. (Pharmacia Corp.); S-Oxide and S,S-dioxide tetrahydrothiopyran phenyloxazolidinones. EP 1036074; US 6083967; WO 9929688 . |
| 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) | 38782 | N-([(5S)-3-[3-fluoro-4-(1-oxo-1,2,3,6-tetrahydro-1lambda(4)-thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide | C17H19FN2O4S | 详情 | 详情 | |
| (II) | 38783 | N-([(5S)-3-[3-fluoro-4-(1-oxohexahydro-1lambda(4)-thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide | C17H21FN2O4S | 详情 | 详情 | |
| (III) | 38785 | N-[[(5S)-3-(3-fluoro-4-tetrahydro-2H-thiopyran-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide | C17H21FN2O3S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)The known dihydrothiopyran derivative (I) was hydrogenated over PtO2 to produce the cis tetrahydrothiopyran sulfoxide (II) along with the trans isomer and the corresponding sulfide, which were separated by column chromatography. Selective hydrolysis of the acetamide function of (II) by means of hydroxylamine and pyridine in EtOH yielded amine (III). This was finally coupled with propionic anhydride to furnish the corresponding propionamide.
| 【1】 Martin, J.P. Jr.; Barbachyn, M.R.; Poel, T.-J. (Pharmacia Corp.); S-Oxide and S,S-dioxide tetrahydrothiopyran phenyloxazolidinones. EP 1036074; US 6083967; WO 9929688 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 17470 | diethyl carbonate; diethylcarbonate | 105-58-8 | C5H10O3 | 详情 | 详情 | |
| (I) | 38782 | N-([(5S)-3-[3-fluoro-4-(1-oxo-1,2,3,6-tetrahydro-1lambda(4)-thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide | C17H19FN2O4S | 详情 | 详情 | |
| (II) | 38783 | N-([(5S)-3-[3-fluoro-4-(1-oxohexahydro-1lambda(4)-thiopyran-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)acetamide | C17H21FN2O4S | 详情 | 详情 | |
| (III) | 38784 | (5S)-5-(aminomethyl)-3-[3-fluoro-4-(1-oxohexahydro-1lambda(4)-thiopyran-4-yl)phenyl]-1,3-oxazolidin-2-one | C15H19FN2O3S | 详情 | 详情 |