Citric Acid → 3-(4-{[4-(Diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoic acid

HRID 508092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508092
[C:1]1([CH:7]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[C:17]([F:28])[CH:16]=3)=[CH:11][C:10]=2[CH2:31][CH:32]([CH3:34])[CH3:33])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[C:35]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][C:9]2[CH:30]=[CH:29][C:12]([CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[C:17]([F:28])[CH:16]=3)=[CH:11][C:10]=2[CH2:31][CH:32]([CH3:33])[CH3:34])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 23157631Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoate

Produkt 1

HCID 231572213-(4-{[4-(Diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl]amino}-2-fluorophenyl)propanoate (0.50 g, 0.93 mmol) in a mixture of methanol (8 mL) and tetrahydrofuran (8 mL) was added an aqueous solution (4 mL) of 85% potassium hydroxide (0.20 g, 3.03 mmol), and the mixture was stirred at room temperature for 18 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 magnesium sulfate, and concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate-diethyl ether to give the title compound (354 mg, yield 75%) as colorless prism crystals.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was recrystallized from ethyl acetate-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6044eade1a394e27a6fe983d9909672d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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