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碘化钠 → benzhydryl (5R,6R,7R)-7-[[(2Z)-2-[5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-(iodomethyl)-5,8-dioxo-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 525920
笔记
打印预览

反应方程式

HRID 525920 反应方程式
[C:1]([O:5][C:6](=[O:58])[C:7]([O:10]/[N:11]=[C:12](/[C:44]1[N:45]=[C:46]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[S:47][C:48]=1[Cl:49])\[C:13]([NH:15][C@@H:16]1[C:23](=[O:24])[N:22]2[C@@H:17]1[S@:18](=[O:43])[CH2:19][C:20]([CH2:41]Cl)=[C:21]2[C:25]([O:27][CH:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:14])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[I-:59].[Na+]>CC(C)=O>[C:1]([O:5][C:6](=[O:58])[C:7]([O:10]/[N:11]=[C:12](/[C:44]1[N:45]=[C:46]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[S:47][C:48]=1[Cl:49])\[C:13]([NH:15][C@@H:16]1[C:23](=[O:24])[N:22]2[C@@H:17]1[S@:18](=[O:43])[CH2:19][C:20]([CH2:41][I:59])=[C:21]2[C:25]([O:27][CH:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:14])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]
参与物实验过程后处理来源与证据反应笔记

参与物

4

反应物 2

HCID 5238碘化钠HCID 90373324benzhydryl (5R,6R,7R)-3-(chloromethyl)-7-[[(2Z)-2-[5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetyl]amino]-5,8-dioxo-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

产物 1

HCID 89488649benzhydryl (5R,6R,7R)-7-[[(2Z)-2-[5-chloro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-(iodomethyl)-5,8-dioxo-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
收率 67.4%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

实验过程

To a solution of (5R,6R,7R)-benzhydryl 7-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)acetamido)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5-oxide (10.5 g, 11.50 mmol) in acetone (120 mL) was added sodium iodide (2.58 g, 17.24 mmol). The mixture was stirred at room temperature over 1.5 h. LCMS indicated completion of the reaction. The solid was filtered off, the filtrate was concentrated under vacuum, the residue was purified twice by CombiFlash Rf automated silica gel chromatography (120 g column), eluting with EtOAc/Hexanes (0-45%) to afford (5R,6R,7R)-benzhydryl 7-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)-5-chlorothiazol-4-yl)acetamido)-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5-oxide (7.5 g, 7.75 mmol, 67.4% yield) as a light brown foaming solid. LCMS: (M+H)+: 967.9.

后处理

  1. customcompletion of the reaction
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated under vacuum
  4. customthe residue was purified twice by CombiFlash Rf automated silica gel chromatography (120 g column)
  5. washeluting with EtOAc/Hexanes (0-45%)

来源与证据

ORD记录
ord-ba112a7a3ff54332bd84caeddeddee8b
来源数据集
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09340556B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记