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【结 构 式】 
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【药物名称】VRC-3885 【化学名称】N-[3-[3-Fluoro-4-(1-oxothiomorpholin-4-yl)phenyl]-2-oxooxazolidin-5(S)-ylmethyl]-3-[4-(methoxyiminomethyl)phenyl]-2-propenamide 【CA登记号】 【 分 子 式 】C25H27FN4O5S 【 分 子 量 】514.58014 |
【开发单位】Vicuron Pharmaceuticals (Originator) 【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Oxazolidinones |
合成路线1
The title compound is prepared by solid phase synthesis utilizing a chloro-derivatized Sasrin resin. Coupling of aminomethyl oxazolidinone (I) to the chloromethyl resin affords the amine bound resin (II). This is then acylated with the cinnamic acid derivative (III) by means of HATU to furnish the corresponding amide (IV). Finally, cleavage of the target amide from resin (IV) is effected by treatment with 10% trifluoroacetic acid in CH2Cl2.
| 【1】 Zhou, J.; et al.; Combinatorial lead optimization of oxazolidinones: In vitro activity of novel 5-amidomethyl thiomorpholine S-oxide and S,S-dioxide phenyloxazolidiones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1319. |
| 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) | 56308 | 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}-1lambda~4~,4-thiazinan-1-one | C14H18FN3O3S | 详情 | 详情 | |
| (II) | 56308 | 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl}-1lambda~4~,4-thiazinan-1-one | C14H18FN3O3S | 详情 | 详情 | |
| (III) | 62247 | (E)-3-{4-[(methoxyimino)methyl]phenyl}-2-propenoic acid | C11H11NO3 | 详情 | 详情 | |
| (IV) | 62248 | (E)-N-({(5S)-3-[3-fluoro-4-(1-oxo-1lambda~4~,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-3-{4-[(methoxyimino)methyl]phenyl}-2-propenamide | C25H27FN4O5S | 详情 | 详情 |