Chloride → 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-[(E)-2-chloroethenyl]benzenesulfonyl]-2-piperazinone

HRID 1840598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840598
[Cl-].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH2:18][C:17]2=[O:33])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[CH:34](Cl)(Cl)[Cl:35].C(OCC)(=O)C>C1COCC1>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:26]=[CH:27][C:28](/[CH:31]=[CH:34]/[Cl:35])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:18][C:17]2=[O:33])[CH2:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:5]

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 6212ChloroformHCID 8857Ethyl AcetateHCID 177986001-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone

Produkt 1

HCID 865866061-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-[(E)-2-chloroethenyl]benzenesulfonyl]-2-piperazinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of chromiun (II) chloride (737 mg) in THF (10 ml) was added a solution of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone (466 mg) and chloroform (0.160 ml) in THF (7 ml), and the mixture was refluxed for 1 hour. To the reaction solution was added ethyl acetate, and the mixture was washed with water and saturated brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give colorless crystals of the title compound (235 m g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 hour
  2. washthe mixture was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-fd17a1dd014f4d79852326f5bc888cb9
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680312B2

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