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Hydrochloric Acid → (4'-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2'-methyl-biphenyl-4-yl)-acetic Acid

HRID 546896
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546896
[OH-].[Na+].C[O:4][C:5](=[O:40])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:26]([CH3:38])[CH:25]=3)([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][C:14]=2[CH3:39])=[CH:9][CH:8]=1.Cl>CO.O1CCCC1>[CH3:36][C:33]([CH3:34])([CH3:35])[C:32](=[O:37])[CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:19]([C:16]2[CH:17]=[CH:18][C:13]([C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C:5]([OH:40])=[O:4])=[CH:12][CH:11]=3)=[C:14]([CH3:39])[CH:15]=2)([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:25][C:26]=1[CH3:38]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57709089(4'-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

Produkt 1

HCID 57708918(4'-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2'-methyl-biphenyl-4-yl)-acetic AcidAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815
MeOH tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A 1 N sodium hydroxide aqueous solution (0.296 mL, 0.296 mmol) was added to a solution of (4′-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 50-(1); 50.7 mg, 0.099 mmol) in methanol-tetrahydrofuran (1:1, 4 mL), and the mixture was stirred at 60° C. for two hours. The reaction mixture was then poured into 0.5 N hydrochloric acid aqueous solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform:methanol=10:1) to give the target compound as a colorless oil (43.3 mg, 87%).

Aufarbeitung

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-46ba09f2db9742a09fbeddf8c69760eb
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935688B2

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