m-Chloroperbenzoic acid → HCID 57736442, compound

HRID 1641739Notes

Reaction equation

HRID 1641739 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:10]1[C:11]([CH3:22])=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH2:20][OH:21])=[O:17])=[N:14][CH:15]=1.ClC1C=CC=C(C(OO)=[O:39])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:23]([C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)=[O:39])[C:10]1[C:11]([CH3:22])=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH2:20][OH:21])=[O:17])=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57736468HCID 57736468, compound

Product 1

HCID 57736442HCID 57736442, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)thio]methyl]-N-(2-hydroxyethyl)-4-methylpyridine-2-carboxamide (478 mg, 1.11 mmol) in methylene chloride (15 ml), 3-chloroperbenzoic acid (293 mg, 1.11 mmol) was added at 0° C. After stirring for 3 hours at the same temperature, the reaction mixture was washed with 1 N aqueous sodium hydroxide, the organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography, and the fraction obtained from an elution with hexane:ethyl acetate=1:2 was concentrated under reduced pressure. The resulting residue was washed with hexane, and then the residue was dried under reduced pressure, to obtain the title compound (238 mg, 0.53 mmol, 48%) as a colorless foamy substance.

Workup

  1. washthe reaction mixture was washed with 1 N aqueous sodium hydroxide
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe fraction obtained from an elution with hexane
  6. concentrationethyl acetate=1:2 was concentrated under reduced pressure
  7. washThe resulting residue was washed with hexane
  8. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-c50140f104f74fb3b3d6828c38f2ee6f
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

Loading…