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4-Toluenesulfonyl chloride → 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-methyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate

HRID 70591
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 70591
Cl.CN(C)C.[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[Cl:17][C:18]1[CH:19]=[C:20](/[C:29](/[C:36]2[NH:41][C:40](=[O:42])[C:39]([CH3:43])=[CH:38][CH:37]=2)=[CH:30]\[CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:21]=[CH:22][C:23]=1[S:24][CH2:25][CH2:26][CH2:27][OH:28].CN(C)CCN>C(Cl)(Cl)Cl.O.C(N(CC)CC)C>[CH3:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:28][CH2:27][CH2:26][CH2:25][S:24][C:23]2[CH:22]=[CH:21][C:20](/[C:29](/[C:36]3[NH:41][C:40](=[O:42])[C:39]([CH3:43])=[CH:38][CH:37]=3)=[CH:30]\[CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:19][C:18]=2[Cl:17])(=[O:15])=[O:14])=[CH:9][CH:8]=1
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Komponenten

8

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 66053N,N-DimethylethylenediamineHCID 10313079Trimethylamine HydrochlorideHCID 584526356-[(E)-1-{3-chloro-4-[(3-hydroxypropyl)sulfanyl]phenyl}-2-cyclopentylethenyl]-3-methylpyridin-2(1H)-one

Produkt 1

HCID 866580093-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-methyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate
Ausbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Triethylamine (148 μL), trimethylamine hydrochloride (50 mg) and 4-methylbenzenesulfonyl chloride (74 mg) were sequentially added to a solution of 6-[(E)-1-{3-chloro-4-[(3-hydroxypropyl)sulfanyl]phenyl}-2-cyclopentylethenyl]-3-methylpyridin-2(1H)-one obtained in Example 1-22 (143 mg) in chloroform (5 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. Water and N,N-dimethylethylenediamine were added to the reaction solution, followed by extraction with chloroform. The organic layer was sequentially washed with 1 M hydrochloric acid and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1→1:1) to give 3-({2-chloro-4-[(E)-2-cyclopentyl-1-(5-methyl-6-oxo-1,6-dihydropyridin-2-yl)ethenyl]phenyl}sulfanyl)propyl 4-methylbenzenesulfonate (33 mg, 18%) as a colorless amorphous.

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was sequentially washed with 1 M hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-89ee4b6c089143c485e83945cc23c6db
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822503B2

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