Sodium Hydroxide → HCID 69072342, Verbindung

HRID 1870008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870008
C([O:3][C:4](=[O:35])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[C:22]3[CH:21]([N:28]([CH:30]4[CH2:32][CH2:31]4)[CH3:29])[CH2:20][CH2:19][C:18]([CH3:34])([CH3:33])[C:17]=3[CH:16]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO.O1CCCC1>[CH:25]1([C:23]2[C:22]3[CH:21]([N:28]([CH:30]4[CH2:31][CH2:32]4)[CH3:29])[CH2:20][CH2:19][C:18]([CH3:33])([CH3:34])[C:17]=3[CH:16]=[C:15]([C:14]#[C:13][C:10]3[CH:9]=[CH:8][C:7]([CH:6]=[CH:5][C:4]([OH:35])=[O:3])=[CH:12][CH:11]=3)[CH:24]=2)[CH2:27][CH2:26]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 69075690HCID 69075690, Verbindung2×

Produkt 1

HCID 69072342HCID 69072342, VerbindungAusbeute 53,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-{4-[4-cyclopropyl-5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acrylic acid ethyl ester (Intermediate 164, 0.08 g, 0.17 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) was treated with 2M sodium hydroxide solution (2 mL, 4 mmol) and the resulting reaction mixture was refluxed overnight. The reaction mixture was cooled to ambient temperature, the volatiles were evaporated in vacuo, the residue was diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a solid. Preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase afforded the title product as a solid (0.04 g, 50%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customthe volatiles were evaporated in vacuo
  4. additionthe residue was diluted with saturated aqueous ammonium chloride solution
  5. extractionextracted with ethyl acetate (×2)
  6. extractionThe combined organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a solid

Quellen und Nachweise

ORD-Eintrag
ord-a708d6db29344043ac657ccf9ea042a6
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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