Sodium Hydroxide → 4-(tert-butyl)-N-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(2-hydroxyethoxy)-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

HRID 1062793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062793
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([N:20](S(C2C=CC(C(C)(C)C)=CC=2)(=O)=O)[S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[N:10]([CH2:47][CH2:48][O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[N:9]=1)(=O)C.[OH-].[Na+]>C(O)C>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([S:21]([NH:20][C:11]2[N:10]([CH2:47][CH2:48][O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[N:9]=[C:8]([O:7][CH2:6][CH2:5][OH:4])[C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:22])=[O:23])=[CH:29][CH:28]=1)([CH3:31])([CH3:32])[CH3:33]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 222820282-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1-{2-([tert-butyl(dimethyl)silyl]oxy}ethyl}4-{4-methylphenyl}-1H-pyrazol-3-yl]oxy}ethyl acetate

Produkt 1

HCID 234003144-(tert-butyl)-N-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(2-hydroxyethoxy)-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamideAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino}-1-{2-{[tert-butyl(dimethyl)silyl]oxy}ethyl}-4-{4-methylphenyl}-1H-pyrazol-3-yl]oxy}ethyl acetate (300 mg) (Preparation 29) and 1.0M sodium hydroxide solution (2 ml) in ethanol (20 ml) was stirred at room temperature overnight. The reaction mixture was evaporated in vacuo and the residue was then diluted with 1.0M citric acid (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a Biotage Flash™ 12i column at 10 psi using 25% ethyl acetate/hexane as eluent to give the title compound as a colourless oil (105 mg).

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. additionthe residue was then diluted with 1.0M citric acid (50 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a Biotage Flash™ 12i column at 10 psi

Quellen und Nachweise

ORD-Eintrag
ord-d79d0ba318264b8680bb8a2de19d3222
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962923B2

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