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【结 构 式】 
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【分子编号】39844 【品名】benzhydryl (6R,7R)-3-[[(aminocarbonyl)oxy]methyl]-7-[[(Z)-1-methoxy-2-(2-thienyl)ethylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C29H27N3O6S2 【 分 子 量 】577.682 【元素组成】C 60.3% H 4.71% N 7.27% O 16.62% S 11.1% |
合成路线1
该中间体在本合成路线中的序号：(XXIX)By reaction of acylated ester (XXVIII) with PCl5 and methanol in CH2Cl2 is converted into benzhydryl-3-carbamoyloxymethyl-7beta-[1-methoxy-2-(2-thienyl)ethylideneamino]-3-cephem-4-carboxylate (XXIX). The methoxylation of (XXIX) in the 7 position is performed either by reaction with phenyllithium and bis(methyl)peroxide in THF [or with phenyllithium and N-bromosuccinimide to the bromo intermediate (XXXI), which is then treated with silver oxide in methanol] yielding, in both cases, the benzhydryl ester of cefoxitin (XXX). Finally, this compound is hydrolyzed with trifluoroacetic acid.
| 【1】 Castaner, J.; Loren, J.G.; Cefoxitin. Drugs Fut 1978, 3, 6, 434. |
| 【2】 Christensen, B.G.; Cama, L.D. (Merck & Co., Inc.); Process for preparing penicillin and cephalosporin compounds. FR 2163144; GB 1401060; US 3843641 . |
| 【3】 Hazen, G.C. (Merck & Co., Inc.); Process for preparin cephalosporin compounds. DD 100957; ES 408969; US 3780033 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXVIII) | 39841 | benzhydryl (6R,7R)-3-[[(aminocarbonyl)oxy]methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C28H25N3O6S2 | 详情 | 详情 | |
| (XXIX) | 39844 | benzhydryl (6R,7R)-3-[[(aminocarbonyl)oxy]methyl]-7-[[(Z)-1-methoxy-2-(2-thienyl)ethylidene]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C29H27N3O6S2 | 详情 | 详情 | |
| (XXX) | 39845 | benzhydryl (6R,7S)-3-[[(aminocarbonyl)oxy]methyl]-7-bromo-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C28H24BrN3O6S2 | 详情 | 详情 | |
| (XXXI) | 39843 | benzhydryl (6R,7S)-3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C29H27N3O7S2 | 详情 | 详情 |