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【结 构 式】 
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【分子编号】48472 【品名】benzhydryl (6R,7R)-7-([2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-[(trityloxy)imino]acetyl]amino)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C47H40ClN5O6S3 【 分 子 量 】902.5154 【元素组成】C 62.55% H 4.47% Cl 3.93% N 7.76% O 10.64% S 10.66% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)Alternatively, derivative (XV) can be obtained from the corresponding mesylate derivative: Treatment of alcohol (I) with MsCl and Et3N in CH2Cl2 yields methansulfonyl derivative (XVI), which is then converted into mesylated aminochlorocephalosporanic acid derivative (XVII) by following these steps: First treatment with metachloroperbenzoic acid (MCPBA) in dichloromethane, followed by reaction with KI and Tf2O in acetonitrile, chlorination with PCl5 and pyridine in dichloromethane, treatment with iBuOH and acidic treatment with TosOH. Condensation of derivative (XVII) with 7-chlorothiazole derivative (VII) by means of (PhO)2POCl in THF provides acetamido derivative (XVIII), which is then treated with chloropyridine derivative (XIV) and NaSH in DMF in DMF to afford compound (XV).
| 【1】 Glinka, T.W.; et al.; SAR studies of anti-MRSA non-zwitterionic 3-heteroarylthiocephems. J Antibiot 2000, 53, 10, 1045. |
| 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 | |
| (VII) | 48463 | 2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-[(trityloxy)imino]acetic acid | C24H18ClN3O3S | 详情 | 详情 | |
| (XIV) | 48468 | tert-butyl 2-[[(4-chloro-2-pyridinyl)methyl]sulfanyl]ethylcarbamate | C13H19ClN2O2S | 详情 | 详情 | |
| (XV) | 48469 | benzhydryl (6R,7R)-7-([2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-[(trityloxy)imino]acetyl]amino)-3-([2-[([2-[(tert-butoxycarbonyl)amino]ethyl]sulfanyl)methyl]-4-pyridinyl]sulfanyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C57H52ClN7O7S4 | 详情 | 详情 | |
| (XVI) | 48470 | benzhydryl (6R,7R)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C31H30N2O5S2 | 详情 | 详情 | |
| (XVII) | 48471 | (6R,7R)-2-[(benzhydryloxy)carbonyl]-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-aminium 4-methylbenzenesulfonate | C30H32N2O7S3 | 详情 | 详情 | |
| (XVIII) | 48472 | benzhydryl (6R,7R)-7-([2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-[(trityloxy)imino]acetyl]amino)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C47H40ClN5O6S3 | 详情 | 详情 |