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【结 构 式】 
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【分子编号】59787 【品名】5-[[3,5-di(tert-butyl)-4-(methoxymethoxy)phenyl](hydroxy)methyl]-2-ethyl-1lambda~6~-isothiazolidine-1,1-dione 【CA登记号】 |
【 分 子 式 】C22H37NO5S 【 分 子 量 】427.60552 【元素组成】C 61.8% H 8.72% N 3.28% O 18.71% S 7.5% |
合成路线1
该中间体在本合成路线中的序号：(V)The intermediate gamma-sultam (III) was prepared by condensation of 3-chloropropylsulfonyl chloride (I) with ethylamine, followed by cyclization of the resulting chloro sulfonamide (II) under basic conditions. Condensation of 3,5-di-tert-butyl-4-(methoxymethoxy)benzaldehyde (IV) with sultam (III) in the presence of LDA produced the aldol addition compound (V). Then, acid-promoted dehydration and simultaneous methoxymethyl group deprotection gave rise to a mixture of the desired E-benzylidene sultam and the corresponding Z-isomer (VII), which were separated by column chromatography.
| 【1】 Inagaki, M.; Tsuri, T.; Jyoyama, H.; yamada, K.; Ono, T.; Matsumoto, S.; A novel antiarthritic agent S-2474: Synthesis and pharmacological effects. 17th Symp Med Chem (Nov 19 1997, Tsukuba) 1997, Abst 2-P-25. |
| 【2】 Matsumoto, S.; Tsuri, T.; Inagaki, M.; Jyoyama, H. (Shionogi & Co. Ltd.); Benzylidene derivs.. EP 0595546; JP 1994211819; US 5418230 . |
| 【3】 Inagaki, M.; Tsuri, T.; Jyoyama, H.; et al.; Novel antiarthritic agents with 1,2-isothiazolidine-1,1-dioxide (gamma-sultam) skeleton: Cytokine suppressive dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase. J Med Chem 2000, 43, 10, 2040. |
| 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) | 39225 | g-Chloropropanesulfonyl chloride;3-Chloropropansulfonyl chloride;1-Chloro-3-propanesulfonylchloride;3-Chloropropanesulfonyl chloride;3-chloro-1-propanesulfonyl chloride;3-chloropropane-1-sulfonyl chloride | 1633-82-5 | C3H6Cl2O2S | 详情 | 详情 |
| (II) | 59784 | 3-chloro-N-ethyl-1-propanesulfonamide | C5H12ClNO2S | 详情 | 详情 | |
| (III) | 59785 | 2-ethyl-1lambda~6~-isothiazolidine-1,1-dione | C5H11NO2S | 详情 | 详情 | |
| (IV) | 59786 | 3,5-di(tert-butyl)-4-(methoxymethoxy)benzaldehyde | C17H26O3 | 详情 | 详情 | |
| (V) | 59787 | 5-[[3,5-di(tert-butyl)-4-(methoxymethoxy)phenyl](hydroxy)methyl]-2-ethyl-1lambda~6~-isothiazolidine-1,1-dione | C22H37NO5S | 详情 | 详情 | |
| (VII) | 59788 | 5-{(Z)-[3,5-di(tert-butyl)-4-hydroxyphenyl]methylidene}-2-ethyl-1lambda~6~-isothiazolidine-1,1-dione | C20H31NO3S | 详情 | 详情 |