tert-Butyl hydroperoxide → 2-[2-[2-(tert-Butoxycarbonylamino)ethoxy)-4-methylsulfinylbenzoylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	tert-Butyl hydroperoxide	HCID 6410	—
Reactant	Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-	HCID 18462	—
Reactant	2-[2-[2-(tert-Butoxycarbonylamino)ethoxy]-4-(methylthio)benzoylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide	HCID 68533941	—
Product	2-[2-[2-(tert-Butoxycarbonylamino)ethoxy)-4-methylsulfinylbenzoylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide	HCID 68534264	212.8%

Reaction Steps

To a solution of 2-[2-[2-(tert-butoxycarbonylamino)ethoxy]-4-(methylthio)-benzoylamino]-N-(5-chloropyridin-2-yl)-5-chlorobenzamide (893 mg, 1.51 mmol), camphorsulfonic acid (92 mg, 0.40 mmol) and CHCl3 (8.5 mL) was added tert-butyl hydroperoxide (0.30 mL, 3.02 mmol). After stirring overnight, the mixture was chromatographed (10% EtOAc/CH2Cl2 to 10% MeOH/CH2Cl2) to give the desired product as a white solid (517 mg, 56%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07700628B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-412e97dd3c244db3b28c35480c935bbf
Source note	uspto-grants-2010_04