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

HRID 1271299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271299
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0e74e201fa374a43848a5119d243e272
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205302B2

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