Citric Acid → 3-{4-[[(2',6'-Dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoic acid

HRID 508022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508022
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH2:29][CH2:30][CH3:31])[C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=2)[CH:10]=1.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH2:29][CH2:30][CH3:31])[C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23157276Methyl 3-{4-[[(2',6'-dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoate

Produkt 1

HCID 231572523-{4-[[(2',6'-Dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoic acidAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-{4-[[(2′,6′-dimethylbiphenyl-3-yl)methyl](propyl)amino]phenyl}propanoate (0.735 g, 1.77 mmol) in a mixture of methanol (8 mL) and tetrahydrofuran (8 mL) was added 2 M aqueous sodium hydroxide solution (2.5 mL), and the mixture was stirred at room temperature for 19 hr. Water was added to the reaction mixture, and the mixture was weakly acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-70% ethyl acetate/hexane) to give the title compound (0.710 g, yield 99%) as a yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (20%-70% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-86ae48b9775544089406e92e1cdb102e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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