m-Chloroperbenzoic acid → HCID 178474239, compound

HRID 546586Notes

Reaction equation

HRID 546586 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:29])[CH3:28])[CH:21]=3)[C:12]2=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:39])C=1>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[N:13]([CH2:19][C:20]3[CH:25]=[CH:24][N+:23]([O-:39])=[C:22]([NH:26][C:27](=[O:29])[CH3:28])[CH:21]=3)[C:12]2=[O:30])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 57625977N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)acetamide

Product 1

HCID 178474239HCID 178474239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 370 mg of N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}pyridin-2-yl)acetamide obtained in stage b) of Example 7 in 20 mL of dichloromethane are added, under argon, and with stirring, 704 mg of 3-chloroperbenzoic acid. After stirring for 1 hour 30 minutes at a temperature in the region of 20° C., 156 mg of 3-chloroperbenzoic acid are added. The solution is stirred overnight and then diluted with dichloromethane and washed three times with saturated aqueous sodium hydrogen carbonate solution. The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure. After chromatography on a column of silica, eluting with a dichloromethane/methanol/28% aqueous ammonia mixture (gradient from 100/0 to 90/9/1 by volume), 280 mg of N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}-1-oxidopyridin-2-yl)acetamide are obtained in the form of a yellow wax, the characteristics of which are as follows:

Workup

  1. additionare added
  2. stirringThe solution is stirred overnight
  3. washwashed three times with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washAfter chromatography on a column of silica, eluting with a dichloromethane/methanol/28% aqueous ammonia mixture (gradient from 100/0 to 90/9/1 by volume), 280 mg of N-(4-{[3-(4-tert-butylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]methyl}-1-oxidopyridin-2-yl)acetamide
  8. customare obtained in the form of a yellow wax

Sources & evidence

ORD record
ord-27ea9c50ccc743adb4c859d29722253e
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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