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

HRID 644236Notes

Reaction equation

HRID 644236 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([S:38][CH3:39])[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1)=[O:20])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=[O:42].C(OO)(C)(C)C>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([S:38]([CH3:39])=[O:42])[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1)=[O:20])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 685339412-[2-[2-(tert-Butoxycarbonylamino)ethoxy]-4-(methylthio)benzoylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 685342642-[2-[2-(tert-Butoxycarbonylamino)ethoxy)-4-methylsulfinylbenzoylamino]-5-chloro-N-(5-chloropyridin-2-yl)benzamideYield 212.8%

Procedure

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%).

Workup

  1. customthe mixture was chromatographed (10% EtOAc/CH2Cl2 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-412e97dd3c244db3b28c35480c935bbf
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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