m-Chloroperbenzoic acid → HCID 86597703, compound

HRID 547815Notes

Reaction equation

HRID 547815 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:35][CH:34](SC)[CH2:33]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl[C:43]1C=CC=C(C(OO)=O)C=1.[S:53]([O-:56])(O)=[O:54].[Na+]>ClCCl>[F:40][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:38])([CH3:39])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:33][CH:34]([S:53]([CH3:43])(=[O:56])=[O:54])[CH2:35]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86597704HCID 86597704, compound

Product 1

HCID 86597703HCID 86597703, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.25 g (0.42 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-methyl-phenyl)-6-(3-methylsulfanyl-azetidin-1-yl)-pyridin-3-yl]-N-methyl-isobutyramide in 10 ml dichloromethane were added 206 mg (70%, 0.84 mmol) 3-chloroperbenzoic acid at 0° C. After completed addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 h. An aqueous solution of sodium hydrogensulfite was added and the mixture was stirred for 10 min. Basification with 1 N aqueous sodium hydroxide solution was followed by extraction with three portions of dichloromethane. The combined organic extracts were dried over sodium sulphate and concentrated. Flash column chromatography gave 0.16 g (60%) of the title compound as a white solid.

Workup

  1. additionaddition
  2. stirringthe mixture was stirred for 10 min
  3. extractionBasification with 1 N aqueous sodium hydroxide solution was followed by extraction with three portions of dichloromethane
  4. dry with materialThe combined organic extracts were dried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a4da0a84ea5f4d9ca7184b2c6eede01c
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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