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【结 构 式】 
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【分子编号】22004 【品名】benzhydryl (6R,7R)-7-[[4-bromo-2-(hydroxyimino)-3-oxobutanoyl]amino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C26H22BrN3O6S 【 分 子 量 】584.4473 【元素组成】C 53.43% H 3.79% Br 13.67% N 7.19% O 16.43% S 5.49% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate (I) with 4-bromoacetoacetyl bromide (II) by means of trimethylsilylacetamide in ethyl acetate gives benzhydryl 7-(4-bromoaceto-acetamido)-3-vinyl-3-cephem-4-carboxylate (III), which by reaction with NaNO2 - acetic acid in dichloromethane and then with urea is converted to benzhydryl 7-[4-bromo-2-(hydroxyimino)acetoacetamido]-3-vinyl-3-cephem-4 carboxylate (IV). The cyclization of (IV) with thiourea in dimethylacetamide affords benzhydryl 7-[2-(2-aminothiazol-4-yl) (hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylate (V), which is finally hydrolyzed with trifluoroacetic acid - anisole as usual.
| 【1】 Kawabata, K.; Masugi, T.; Takaya, T.; Taksugi, H.; Yamanaka, H. (Fujisawa Pharmaceutical Co., Ltd.); Syn-isomer of 7-substd.-3-vinyl-3-cephem cpds., pr. EP 0105459; ES 8600309; ES 8800235; US 4559334 . |
| 【2】 Castaner, J.; Prous, J.; FK-482. Drugs Fut 1988, 13, 3, 224. |
| 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) | 22001 | benzhydryl (6R,7R)-7-amino-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C22H20N2O3S | 详情 | 详情 | |
| (II) | 15619 | 5-(acetoxy)-1,3-oxathiolane-2-carboxylic acid | C6H8O5S | 详情 | 详情 | |
| (III) | 22003 | benzhydryl (6R,7R)-7-[(4-bromo-3-oxobutanoyl)amino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C26H23BrN2O5S | 详情 | 详情 | |
| (IV) | 22004 | benzhydryl (6R,7R)-7-[[4-bromo-2-(hydroxyimino)-3-oxobutanoyl]amino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C26H22BrN3O6S | 详情 | 详情 | |
| (V) | 22005 | benzhydryl (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetyl]amino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C27H23N5O5S2 | 详情 | 详情 | |
| (VI) | 63021 | N-(trimethylsilyl)acetamide | 13435-12-6 | C5H13NOSi | 详情 | 详情 |
| (VII) | 19310 | urea | 57-13-6 | CH4N2O | 详情 | 详情 |
| (VIII) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |