Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 15908470, Verbindung

HRID 480024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480024
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:15])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[S:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.Cl[C:39]([N:41]=[C:42]=[O:43])=[O:40]>C1(C)C=CC=CC=1>[O:40]=[C:39]1[N:1]([CH2:2][CH2:3][CH2:4][N:5]([CH3:15])[S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:8])=[O:7])[C:19]2[CH2:18][CH2:17][S:16][CH2:21][C:20]=2[C:42](=[O:43])[NH:41]1

Komponenten

6

Edukt 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 66173Tetrahydrothiopyran-4-oneHCID 119708Isocyanatocarbonyl chlorideHCID 28387092HCID 28387092, Verbindung

Produkt 1

HCID 15908470HCID 15908470, VerbindungAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 0.98 g (4.3 mmol) of N-(3-aminopropyl)-N-methylphenylsulphonamide [preparation according to P. Daetwyler et al., Helv. Chim. Acta, 61, 2646 (1978)], 0.55 g (4.73 mmol) of tetrahydrothiopyran-4-one and a catalytic amount of camphorsulphonic acid in 50 ml of toluene is heated at reflux for 3 hours using a Dean-Stark separator. After cooling to room temperature, the Dean-Stark separator is removed, 0.54 g (5.16 mmol) of chlorocarbonyl isocyanate are added and the mixture is refluxed for another hour. The solvent is removed using a rotary evaporator and the resulting residue is purified by preparative HPLC (RP-C18, acetonitrile/water gradient). This gives 717 mg (42% yield) of an amorphous solid.

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. customthe Dean-Stark separator is removed
  3. temperaturethe mixture is refluxed for another hour
  4. customThe solvent is removed
  5. customa rotary evaporator
  6. customthe resulting residue is purified by preparative HPLC (RP-C18, acetonitrile/water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-59507797d8c1461cb5e256b75799f333
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649618B2

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