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【结 构 式】 
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【药物名称】Lenampicillin hydrochloride, KBT-1585, KB-1585, Takacillin, Veracillin 【化学名称】Ampicillin (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl ester hydrochloride 【CA登记号】80734-02-7, 86273-18-9 (free base) 【 分 子 式 】C21H24ClN3O7S 【 分 子 量 】497.95833 |
【开发单位】Kanebo (Originator), MECT (Originator), Sigma-Tau (Licensee) 【药理作用】Penicillins |
合成路线1
The bromination of 4,5-dimethyl-1,3-dioxolen-2-one (I) with N-bromo-succinimide (NBS) and azobisisobutyronitrile (AIBN) in CCl4 gives 4-methyl-5-bromomethyl-1,3-diioxolen-2-one (II), which is then condensed with ampicillin (III) by means of KHCO3 and benzaldehyde in DMF.
| 【1】 Sakamoto, F.; Ikeda, S.; Tsukamoto, G.; Utsumi, I. (Kanebo Pharmaceuticals, Ltd.); Novel ampicillin esters and production thereof. EP 0039086; EP 0039477; EP 0061206; US 4389408 . |
| 【2】 Serradell, M.N.; Castaner, J.; Blancafort, P.; KB-1585. Drugs Fut 1983, 8, 11, 920. |
| 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) | 31106 | 4,5-dimethyl-1,3-dioxol-2-one | 37830-90-3 | C5H6O3 | 详情 | 详情 |
| (II) | 13462 | 4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one | 80715-22-6 | C5H5BrO3 | 详情 | 详情 |
| (III) | 31107 | (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | 69-53-4 | C16H19N3O4S | 详情 | 详情 |
Extended Information