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【结 构 式】 
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【药物名称】SA-9499 【化学名称】S-(4-Cyclohexylbenzyl)-N-[2(S)-methyl-3-sulfanylpropionyl]- L-cysteine 【CA登记号】 【 分 子 式 】C20H29NO3S2 【 分 子 量 】395.58703 |
【开发单位】Santen 【药理作用】ANTIARTHRITIC DRUGS |
合成路线1
The esterification of 3-(benzoylsulfanyl)-2(S)-methylpropionic acid with 4-nitrophenol (II) by means of DCC in dichloromethane gives the corresponding ester (III), which is condensed with S-(4-cyclohexylbenzyl)-L-cysteine (IV) (obtained by alkylation of L-cysteine (V) with 4-cyclohexylbenzyl bromide (VI)) to yield the corresponding amide (VII). Finally, this compound is debenzoylated by a treatment with aqueous NH4OH.
| 【1】 Horiuchi, M.; Fujimura, K.; Suhara, H. (Santen Pharmaceutical Co., Ltd.); Novel sulfur-containing amino acid derivs.. EP 0947502; JP 1998130225; US 6046235; WO 9809943 . |
| 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) | 35379 | (2S)-3-(benzoylsulfanyl)-2-methylpropionic acid | C11H12O3S | 详情 | 详情 | |
| (II) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |
| (III) | 35380 | 4-nitrophenyl (2S)-3-(benzoylsulfanyl)-2-methylpropanoate | C17H15NO5S | 详情 | 详情 | |
| (IV) | 35381 | (2R)-2-amino-3-[(4-cyclohexylbenzyl)sulfanyl]propionic acid | C16H23NO2S | 详情 | 详情 | |
| (V) | 14643 | L-cysteine; (R)-2-Amino-3-mercaptopropionic acid | 52-90-4 | C3H7NO2S | 详情 | 详情 |
| (VI) | 35382 | 1-(bromomethyl)-4-cyclohexylbenzene | C13H17Br | 详情 | 详情 | |
| (VII) | 35383 | (2R)-2-[[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]amino]-3-[(4-cyclohexylbenzyl)sulfanyl]propionic acid | C27H33NO4S2 | 详情 | 详情 |
Extended Information