Sodium Iodide → HCID 89488638, compound

HRID 525895Notes

Reaction equation

HRID 525895 reaction equation
[C:1]([O:5][C:6](=[O:53])[C:7]([O:10]/[N:11]=[C:12](/[C:40]1[N:41]=[C:42]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[S:43][CH:44]=1)\[C:13]([NH:15][C@@H:16]1[C:23](=[O:24])[N:22]2[C@@H:17]1[S@:18](=[O:39])[CH2:19][C:20]([CH2:37]Cl)=[C:21]2[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:26])=[O:14])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[I-:54].[Na+]>CC(C)=O>[C:1]([O:5][C:6](=[O:53])[C:7]([O:10]/[N:11]=[C:12](/[C:40]1[N:41]=[C:42]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[S:43][CH:44]=1)\[C:13]([NH:15][C@@H:16]1[C:23](=[O:24])[N:22]2[C@@H:17]1[S@:18](=[O:39])[CH2:19][C:20]([CH2:37][I:54])=[C:21]2[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[O:26])=[O:14])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 90373625HCID 90373625, compound

Product 1

HCID 89488638HCID 89488638, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of (5R,6R,7R)-4-methoxybenzyl 7-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5-oxide (5 g, 6.28 mmol) in Acetone (50 mL) was added sodium iodide (1.176 g, 7.85 mmol) and the mixture was stirred at rt for 2 h. Solvent was removed under vacuum, the residue was chromatographed to give (5R,6R,7R)-4-methoxybenzyl 7-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5-oxide (4.5 g, 5.07 mmol, 81% yield). LCMS: (M+H)+: 887.6

Workup

  1. customSolvent was removed under vacuum
  2. customthe residue was chromatographed

Sources & evidence

ORD record
ord-ebea355d528f4f958ea019ddafec5fbe
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

Loading…