tert-Butyl hydroperoxide → HCID 57860769, compound

HRID 644190Notes

Reaction equation

HRID 644190 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40][CH3:41])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[CH:35]=[CH:34][CH:33]=[CH:32][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=[O:44].C(OO)(C)(C)C>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40]([CH3:41])=[O:44])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[CH:35]=[CH:34][CH:33]=[CH:32][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:18])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 57860832HCID 57860832, compound

Product 1

HCID 57860769HCID 57860769, compoundYield 133.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (291 mg, 0.49 mmol) was dissolved in chloroform (2.5 mL). Camphorsulfonic acid (20 mg, 0.09 mmol) was added, followed by t-butyl hydroperoxide solution (0.1 mL, 1.00 mmol). The reaction was stirred overnight and then loaded directly onto a column for flash column chromatographic purification (about 30 g silica, 10% EtOAc/CH2Cl2 through 100% EtOAc). The pure material (75 mg, 0.12 mmol, 25%) was obtained as a white solid.

Workup

  1. customloaded directly onto a column for flash column chromatographic purification (about 30 g silica, 10% EtOAc/CH2Cl2 through 100% EtOAc)

Sources & evidence

ORD record
ord-42a22b56dc1a44bd81cf37c2a1d56739
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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