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【结 构 式】 
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【分子编号】18138 【品名】trifluoro-N-[3-([(2R,3R)-6-[(5-fluoro-1,3-benzothiazol-2-yl)methoxy]-2-methyl-4-oxo-3,4-dihydro-2H-chromen-3-yl]methyl)phenyl]-N-[(trifluoromethyl)sulfonyl]methanesulfonamide 【CA登记号】 |
【 分 子 式 】C27H19F7N2O7S3 【 分 子 量 】712.6439624 【元素组成】C 45.51% H 2.69% F 18.66% N 3.93% O 15.72% S 13.5% |
合成路线1
该中间体在本合成路线中的序号：(XIII)Treatment with triflic anhydride yielded the less polar bis(sulfonamide) (XIII), which could be reduced with NaBH4 in the presence of cerium (III) chloride to afford a mixture of alcohols, from which the desired 3,4-cis alcohol (XIV) was isolated by chromatography. Resolution of racemic (XIV) was achieved by esterification with Boc-D-Tryptophan (XV) on treatment with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and DMAP, followed by chromatographic separation of the resulting diastereoisomeric esters. Finally, hydrolysis of the desired isomer (XVI) with LiOH afforded the (+) enantiomer of the target compound.
| 【1】 Chambers, R.J.; Antognoli, G.W.; Cheng, J.B.; Marfat, A.; Pillar, J.S.; Shirley, J,T,; Watson, J.W.; Development of new chromanol antagonists of leukotriene D4. Bioorg Med Chem Lett 1998, 8, 14, 1791. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 18137 | trifluoro-N-[3-([(2R,3R)-6-[(5-fluoro-1,3-benzothiazol-2-yl)methoxy]-2-methyl-4-oxo-3,4-dihydro-2H-chromen-3-yl]methyl)phenyl]methanesulfonamide | C26H20F4N2O5S2 | 详情 | 详情 | |
| (XIII) | 18138 | trifluoro-N-[3-([(2R,3R)-6-[(5-fluoro-1,3-benzothiazol-2-yl)methoxy]-2-methyl-4-oxo-3,4-dihydro-2H-chromen-3-yl]methyl)phenyl]-N-[(trifluoromethyl)sulfonyl]methanesulfonamide | C27H19F7N2O7S3 | 详情 | 详情 | |
| (XIV) | 18139 | trifluoro-N-[3-([(2R,3S,4R)-6-[(5-fluoro-1,3-benzothiazol-2-yl)methoxy]-4-hydroxy-2-methyl-3,4-dihydro-2H-chromen-3-yl]methyl)phenyl]-N-[(trifluoromethyl)sulfonyl]methanesulfonamide | C27H21F7N2O7S3 | 详情 | 详情 | |
| (XV) | 18140 | (2R)-2-[(tert-butoxycarbonyl)amino]-2-(1H-indol-3-yl)ethanoic acid | C15H18N2O4 | 详情 | 详情 | |
| (XVI) | 18141 | (2R,3R,4R)-3-(3-[bis[(trifluoromethyl)sulfonyl]amino]benzyl)-6-[(5-fluoro-1,3-benzothiazol-2-yl)methoxy]-2-methyl-3,4-dihydro-2H-chromen-4-yl (2R)-2-[(tert-butoxycarbonyl)amino]-2-(1H-indol-3-yl)ethanoate | C42H37F7N4O10S3 | 详情 | 详情 |