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【结 构 式】 
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【药物名称】FR-193879 【化学名称】(6R,7R)-3-[4-(Carbamoylmethyl)thiazol-2-ylsulfanyl]-7-(2-phenylacetamido)-3-cephem-4-carboxylic acid 【CA登记号】194928-82-0 【 分 子 式 】C20H18N4O5S3 【 分 子 量 】490.58226 |
【开发单位】Fujisawa (Originator) 【药理作用】Antibiotics, Anti-Helicobacter Pylori Agents, ANTIINFECTIVE THERAPY, Antiulcer Drugs, GASTROINTESTINAL DRUGS, Cephalosporins |
合成路线1
The reaction of 2-(2-sulfanylthiazol-4-yl)acetic acid ethyl ester (I) with ammonia and ammonium chloride gives the corresponding acetamide (II), which is condensed with the cephem methanesulfonate (III) by means of potassium tert-butoxide in dimethoxyethane to yield the diphenylmethyl ester (IV) of the target compound, which is finally hydrolyzed with trifluoroacetic acid and anisole.
| 【1】 Yoshida, Y.; Okuda, S.; Sasaki, H.; Matsuda, K.; Takasugi, H. (Fujisawa Pharmaceutical Co., Ltd.); New cephem cpds. and pharmaceutical use thereof. EP 0882052; JP 2000505432; WO 9729111 . |
| 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) | 25089 | ethyl 2-(2-sulfanyl-1,3-thiazol-4-yl)acetate | C7H9NO2S2 | 详情 | 详情 | |
| (II) | 25090 | 2-(2-sulfanyl-1,3-thiazol-4-yl)acetamide | C5H6N2OS2 | 详情 | 详情 | |
| (III) | 25091 | benzhydryl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C29H26N2O7S2 | 详情 | 详情 | |
| (IV) | 25092 | benzhydryl (6R,7R)-3-[[4-(2-amino-2-oxoethyl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C33H28N4O5S3 | 详情 | 详情 |
Extended Information