Sodium hydroxide ethanol → N-{2-[3-(3-Benzyl-azetidin-3-yl)-phenoxy]-ethyl}-C-cyclopropyl-methane sulfonamide

HRID 331700

Reaktionsgleichung

Reaktionsgleichung von HRID 331700
C(OC([N:6]1[CH2:9][C:8]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH:24]3[CH2:26][CH2:25]3)(=[O:22])=[O:21])[CH:11]=2)[CH2:7]1)=O)C.[OH-].[Na+].CCO>[Cl-].[Na+].O>[CH2:27]([C:8]1([C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[O:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH:24]2[CH2:25][CH2:26]2)(=[O:22])=[O:21])[CH2:7][NH:6][CH2:9]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 23692425Sodium hydroxide ethanolHCID 667467573-Benzyl-3-[3-(2-cyclopropylmethanesulfonylamino-ethoxy)-phenyl]-azetidine-1-carboxylic acid ethyl ester

Produkt 1

HCID 66746666N-{2-[3-(3-Benzyl-azetidin-3-yl)-phenoxy]-ethyl}-C-cyclopropyl-methane sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To 3-benzyl-3-[3-(2-cyclopropylmethanesulfonylamino-ethoxy)-phenyl]-azetidine-1-carboxylic acid ethyl ester (50 mg, 0.11 mmol) was added 4 ml 2N NaOH/EtOH. The mixture was heated for 1 hour in a microwave. After cooling to room temperature 50% brine was added and the mixture extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium bicarbonate, filtered and the solvent evaporated. The residue was purified on 4 g SiO2 using 10% methanol in dichloromethane affording the desired product as a clear oil. m=15.5 mg

Aufarbeitung

  1. temperatureThe mixture was heated for 1 hour in a microwave
  2. additionwas added
  3. extractionthe mixture extracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium bicarbonate
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified on 4 g SiO2 using 10% methanol in dichloromethane affording the desired product as a clear oil

Quellen und Nachweise

ORD-Eintrag
ord-b45ddf19bd5e48ad84259f297dd38baa
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877794B2

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