Dimethyl Sulfoxide → 1-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone

HRID 1840597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1840597
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][N:25]2[CH2:30][CH2:29][N:28]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][OH:41])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[CH2:27][C:26]2=[O:42])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([CH2:24][N:25]2[CH2:30][CH2:29][N:28]([S:31]([C:34]3[CH:35]=[CH:36][C:37]([CH:40]=[O:41])=[CH:38][CH:39]=3)(=[O:32])=[O:33])[CH2:27][C:26]2=[O:42])[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 177986031-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-(hydroxymethyl)benzenesulfonyl]-2-piperazinone

Produkt 1

HCID 177986001-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinoneAusbeute 108,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

To a solution of oxalyl chloride (0.70 ml) in dichloromethane (60 ml) was added dropwise at −70° C. a solution of dimethylsulfoxide (0.85 ml) in dichloromethane (10 ml). Ten minutes later, to the mixture was added dropwise a solution of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-(hydroxymethyl)benzenesulfonyl]-2-piperazinone (1.87 g) in dichloromethane (20 ml), and the mixture was stirred at about −65° C. for 1 hour. To the mixture was added triethylamine (2.79 ml), and the mixture was stirred at −60° C. to −30° C. for 2 hours. The reaction solution was diluted with dichloromethane, washed with water and saturated brine, dried and concentrated, and the the residue was purified with silica gel column chromatography (ethyl acetate). Precipitated crystals were washed with ether to give colorless crystals of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone (2.02 g).

Aufarbeitung

  1. stirringthe mixture was stirred at −60° C. to −30° C. for 2 hours
  2. washwashed with water and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customthe the residue was purified with silica gel column chromatography (ethyl acetate)
  6. customPrecipitated crystals
  7. washwere washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-830dcc3187b54850900238c5224471f3
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06680312B2

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