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【结 构 式】 
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【分子编号】25091 【品名】benzhydryl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C29H26N2O7S2 【 分 子 量 】578.66672 【元素组成】C 60.19% H 4.53% N 4.84% O 19.35% S 11.08% |
合成路线1
该中间体在本合成路线中的序号：(III)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 |
合成路线2
该中间体在本合成路线中的序号：(II)The title compound has been prepared by two related procedures: Treatment of 3-hydroxy cephem derivative (I) with methanesulfonyl chloride and K2CO3 afforded mesylate (II), which was condensed with 2-mercapto-5-methyl-1,3,4-thiadiazole (III) in the presence of potassium tert-butoxide to give thioether (IV). The benzhydryl ester of (IV) was then deprotected by treatment with trifluoroacetic acid.
| 【1】 Tawara, S.; Sasaki, H.; Matsumoto, S.; Takasugi, H.; Yoshida, Y.; Matsumoto, Y.; Matsuda, K.; Studies of anti-Helicobacter pylori agents. Part 2: New cephem derivatives. Bioorg Med Chem 2000, 8, 9, 2317. |
| 【2】 Sasaki, H.; Takasugi, H.; Matsumoto, Y.; Yoshida, Y.; Matsuda, K.; Matsumoto, s.; Synthesis and anti-Helicobacter pylori activity of FR182024, a new cephem derivative. Bioorg Med Chem Lett 1999, 9, 21, 3123. |
| 【3】 Yoshida, Y.; Sasaki, H.; Matsuda, K.; Takasugi, H. (Fujisawa Pharmaceutical Co., Ltd.); Cephem cpds. and pharmaceutical use thereof. EP 0796263; JP 1998510258; WO 9617850 . |
| 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) | 37977 | benzhydryl (6R,7R)-3-hydroxy-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C28H24N2O5S | 详情 | 详情 | |
| (II) | 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 | |
| (III) | 37978 | 5-methyl-1,3,4-thiadiazole-2-thiol; 5-methyl-1,3,4-thiadiazol-2-ylhydrosulfide | 29490-19-5 | C3H4N2S2 | 详情 | 详情 |
| (IV) | 37979 | benzhydryl (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C31H26N4O4S3 | 详情 | 详情 |