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【结 构 式】 
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【药物名称】Cefotiam cilexetil, Cefotiam hexetil, SCE-2174, Pansporin T 【化学名称】(6R,7R)-7-[2-(2-Amino-4-thiazolyl)acetamido]-3-[[[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(cyclohexyloxycarbonyloxy)ethyl ester 【CA登记号】61622-34-2 【 分 子 式 】C27H37N9O7S3 【 分 子 量 】695.84404 |
【开发单位】Takeda (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Cephalosporins |
合成路线1
The reaction of 1-chloroethyl chloroformate (I) with cyclohexanol (II) by means of pyridine in dichloromethane gives 1-chloroethyl cyclohexyl carbonate (III), which is converted to the corresponding iodoethyl derivative (IV) with NaI in hot acetonitrile. Finaly this compound is condensed with potassium 7beta-[2-(2-aminothiazol-4-yl)acetamido]-3-[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylate (V) in DMF.
| 【1】 Yashiki, T.; Nishimura, T.; Numata, M.; Hirai, S.; Takanohashi, K.; Miyake, A.; Yoshimura, Y.; Hamaguchi, N.; Yamaoka, M.; Orally active 1-(cyclohexyloxycarbonyloxy)alkyl es. J Antibiot 1987, 40, 1, 81. |
| 【2】 Hirai, S.; Koyama, H.; Makino, T. (Takeda Chemical Industries, Ltd.); Antibacterial solid compsn. for oral administratio. EP 0163433; JP 1985233012; JP 1987030713 . |
| 【3】 Castaner, J.; Prous, J.; SCE-2174. Drugs Fut 1988, 13, 3, 231. |
| 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) | 22014 | 1-chloro-1-[(chlorocarbonyl)oxy]ethane | 50893-53-3 | C3H4Cl2O2 | 详情 | 详情 |
| (II) | 11306 | Cyclohexanol | 108-93-0 | C6H12O | 详情 | 详情 |
| (III) | 15573 | 1-chloroethyl cyclohexyl carbonate | C9H15ClO3 | 详情 | 详情 | |
| (IV) | 15339 | cyclohexyl 1-iodoethyl carbonate | 102672-57-1 | C9H15IO3 | 详情 | 详情 |
| (V) | 22018 | potassium (7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-3-[([1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetraazol-5-yl]sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C18H22KN9O4S3 | 详情 | 详情 |