Water → phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylate

HRID 1953445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953445
[NH2:1][C:2]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(OCC)(=O)C>[CH3:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH:1][C:2]2([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)(=[O:40])=[O:39])=[CH:36][CH:37]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 19763929Phenylmethyl 1-aminocyclohexanecarboxylate-p-toluenesulfonate

Produkt 1

HCID 23297905phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

8.1 g (20 mmol) of phenylmethyl 1-aminocyclohexanecarboxylate ·p-toluenesulfonate was added to 50 nm of water, and then 4.1 g (20 mmol) of 4-methoxybenzenesulfonylchloride and 50 ml of ethyl acetate was added to the mixture with stirring. After stirring at room temperature, the reaction mixture was put into a separatory funnel and water layer was removed therefrom. Subsequently, organic layer was washed with successive, 10% potassium hydrogensulfate solution, and saturated brine, and then, was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The obtained crystal was stirred overnight in ether, whereby 4.36 g of phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylate was obtained.

Aufarbeitung

  1. stirringAfter stirring at room temperature
  2. customthe reaction mixture was put into a separatory funnel
  3. customwater layer was removed
  4. washSubsequently, organic layer was washed with successive, 10% potassium hydrogensulfate solution, and saturated brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationthe solvent was concentrated under reduced pressure
  7. stirringThe obtained crystal was stirred overnight in ether

Quellen und Nachweise

ORD-Eintrag
ord-c32a8e12646547849f8b7d52975ba12c
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117870

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