m-Chloroperbenzoic acid → HCID 87304500, compound

HRID 547810Notes

Reaction equation

HRID 547810 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([C:18]2[C:19]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[CH3:41])=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][CH:27]([CH2:30][S:31]([CH3:33])=[O:32])[CH2:26][CH2:25]3)=[N:22][CH:23]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.ClC1C=CC=C(C(OO)=[O:54])C=1.S([O-])(O)=O.[Na+]>ClCCl>[F:45][C:2]([F:1])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:42])([CH3:43])[C:14]([N:16]([C:18]2[C:19]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[CH3:41])=[CH:20][C:21]([N:24]3[CH2:25][CH2:26][CH:27]([CH2:30][S:31]([CH3:33])(=[O:54])=[O:32])[CH2:28][CH2:29]3)=[N:22][CH:23]=2)[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 87304579HCID 87304579, compound

Product 1

HCID 87304500HCID 87304500, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.22 g (0.33 mmol) (RS)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[4′-(4-fluoro-2-methyl-phenyl)-4-methanesulfinylmethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl]-N-methyl-isobutyramide in 5 ml dichloromethane were added 142 mg (70%, 0.58 mmol) 3-chloroperbenzoic acid at 0° C. After completed addition, the reaction mixture was allowed to warm to room temperature and stirred over night. 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 0.13 g (55%) 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-f2d69a1cd6944aa39719dc2db92f43ea
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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