m-Chloroperbenzoic acid → 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butylsulfinyl]acetic Acid Methyl Ester

HRID 1271299Notes

Reaction equation

HRID 1271299 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][S:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]([C:14]1[CH:19]=[N:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:15]=1)[CH:11]([CH3:13])[CH3:12].ClC1C=C(C=CC=1)C(OO)=[O:38]>ClCCl.C(=O)([O-])O.[Na+]>[CH3:1][O:2][C:3](=[O:32])[CH2:4][S:5]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]([C:14]1[CH:19]=[N:18][C:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:15]=1)[CH:11]([CH3:13])[CH3:12])=[O:38]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 693549872-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butylthio}acetic Acid Methyl Ester

Product 1

HCID 693553172-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butylsulfinyl]acetic Acid Methyl EsterYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 600 mg of 2-{4-[N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino]butylthio}acetic acid methyl ester obtained in Example 36 in 10 ml of dichloromethane was ice-cooled and 329 mg of 70% m-chloroperoxybenzoic acid was added. After stirring under ice cooling for 2 hours, the reaction solution was diluted with an aqueous saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 385 mg of the desired compound as a yellowish crystal having a melting point of 128 to 130° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0e74e201fa374a43848a5119d243e272
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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