m-Chloroperbenzoic acid → HCID 58009488, compound

HRID 1009486Notes

Reaction equation

HRID 1009486 reaction equation
[Cl:1][C:2]1[C:3]([CH3:30])=[C:4]([N:8]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:39])C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:30])=[C:4]([N:8]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)(=[O:21])=[O:22])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][N+:17]([O-:39])=[CH:18][CH:19]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 51344618HCID 51344618, compound

Product 1

HCID 58009488HCID 58009488, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

330 mg of N2-(3-chloro-2-methylphenyl)-N2-[(4-methylphenyl)sulfonyl]-N-(pyridine-4-ylmethyl)glycinamide was dissolved in 5.0 mL of methylene chloride, and 166 mg of m-chloroperbenzoic acid was added thereto, followed by stirring at room temperature for 4 hours. To the reaction liquid was added an aqueous saturated sodium hydrogen carbonate solution, and then extracted with chloroform. The organic layer was concentrated under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform:methanol=99:1), and the obtained residue was crystallized from hexane/ethyl acetate to obtain 179 mg of N2-(3-chloro-2-methylphenyl)-N2-[(4-methylphenyl)sulfonyl]-N-[(1-oxidopyridine-4-yl)methyl]glycinamide.

Workup

  1. customTo the reaction liquid
  2. extractionextracted with chloroform
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=99:1)
  5. customthe obtained residue was crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-c7e5661fdfb14b16bb920bf0c5b23777
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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