HRID525849

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID5238

Sodium Iodide

INa

$结构：COc1ccc(COC(=O)C2=C(CCl)C[S@@](=O)[C@@H]3[C@H](NC(=O)/C(=N\O[C@@H](CC(=O)OC(C)(C)C)C(=O)OCc4ccc(OC)cc4)c4csc(NC(=O)OC(C)(C)C)n4)C(=O)N23)cc1$

HCID90373487

未命名化合物

PRODUCTS

生成物

$结构：COc1ccc(COC(=O)C2=C(CI)C[S@@](=O)[C@@H]3[C@H](NC(=O)/C(=N\O[C@@H](CC(=O)OC(C)(C)C)C(=O)OCc4ccc(OC)cc4)c4csc(NC(=O)OC(C)(C)C)n4)C(=O)N23)cc1$

HCID89488533

未命名化合物

收率 85%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID180

Acetone

C3H6O

PROCEDURE

实验过程

To the solution of (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((5R,6R,7R)-3-(chloromethyl)-2-(((4-methoxybenzyl)oxy)carbonyl)-5-oxido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl)amino)-2-oxoethylidene)amino)oxy)succinate (1.183 g, 1.25 mmol) in acetone (50 mL) at room temperature was added sodium iodide (0.234 g, 1.563 mmol). The mixture stirred at room temperature for 2 hours. Filtered and evaporated to give (S)-4-tert-butyl 1-(4-methoxybenzyl) 2-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-(((5R,6R,7R)-3-(iodomethyl)-2-(((4-methoxybenzyl)oxy)carbonyl)-5-oxido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl)amino)-2-oxoethylidene)amino)oxy)succinate (1.1 g, 1.060 mmol, 85% yield). LCMS (M+H)+: 1038.9

WORKUP

后处理

filtrationFiltered
customevaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bd700d9e61ce4e1f8126f3e52961404d
来源数据集: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09340556B2
来源说明: uspto-grants-2016_05

反应 SMILES

[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:42]/[O:43][C@@H:44]([CH2:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)=[O:46])/[C:15]([NH:17][C@@H:18]2[C:25](=[O:26])[N:24]3[C@@H:19]2[S@:20](=[O:41])[CH2:21][C:22]([CH2:39]Cl)=[C:23]3[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[O:28])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-:65].[Na+]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:42]/[O:43][C@@H:44]([CH2:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)=[O:46])/[C:15]([NH:17][C@@H:18]2[C:25](=[O:26])[N:24]3[C@@H:19]2[S@:20](=[O:41])[CH2:21][C:22]([CH2:39][I:65])=[C:23]3[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)=[O:28])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]