Sodium Hydroxide → (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic Acid

HRID 547030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547030
[OH-].[Na+].C[O:4][C:5](=[O:40])[CH2:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:38][CH3:39])([C:23]3[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([CH2:35][CH3:36])([OH:34])[CH2:32][CH3:33])=[C:25]([CH3:37])[CH:24]=3)[CH2:21][CH3:22])=[CH:16][CH:15]=2)[CH:10]=[C:11]([F:13])[CH:12]=1.[Cl-].[NH4+]>CO.O1CCCC1>[CH2:21]([C:20]([C:17]1[CH:16]=[CH:15][C:14]([C:9]2[CH:10]=[C:11]([F:13])[CH:12]=[C:7]([CH2:6][C:5]([OH:40])=[O:4])[CH:8]=2)=[CH:19][CH:18]=1)([C:23]1[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([CH2:32][CH3:33])([OH:34])[CH2:35][CH3:36])=[C:25]([CH3:37])[CH:24]=1)[CH2:38][CH3:39])[CH3:22]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57709075(4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic Acid Methyl Ester

Produkt 1

HCID 57709139(4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic AcidAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

A 1 N sodium hydroxide aqueous solution (0.335 mL, 0.335 mmol) was added to a solution of (4′-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-5-fluoro-biphenyl-3-yl)-acetic acid methyl ester (Example 127-(2); 57.7 mg, 0.112 mmol) in methanol-tetrahydrofuran (1:1, 4 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into a saturated aqueous ammonium chloride 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 (38.5 mg, 68%).

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-c15a6fbae8b34caaa7162be85b2dcfb4
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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