Hydrochloric Acid → (4E)-4-phenyl-4-[[4-[(5-phenylimidazo[1,2-a]pyridin-2-yl)methoxy]phenyl]methoxyimino]butanoic acid

HRID 1070131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070131
[OH-].[Na+].[C:3]1([C:9]2[N:14]3[CH:15]=[C:16]([CH2:18][O:19][C:20]4[CH:41]=[CH:40][C:23]([CH2:24][O:25]/[N:26]=[C:27](/[C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)\[CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:22][CH:21]=4)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.Cl>O1CCCC1>[C:3]1([C:9]2[N:14]3[CH:15]=[C:16]([CH2:18][O:19][C:20]4[CH:21]=[CH:22][C:23]([CH2:24][O:25]/[N:26]=[C:27](/[C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)\[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:40][CH:41]=4)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 22344624HCID 22344624, Verbindung

Produkt 1

HCID 22344572(4E)-4-phenyl-4-[[4-[(5-phenylimidazo[1,2-a]pyridin-2-yl)methoxy]phenyl]methoxyimino]butanoic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 1N aqueous saturated solution of sodium hydroxide (5 ml) was added to a solution of methyl E-4-[4-(5-phenylimidazo[1,2-α]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyrate (400 mg) in tetrahydrofuran (10 ml)-methanol (5 ml) and stirred at room temperature for 1 hour. 1N hydrochloric acid (5.5 ml) was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain E-4-[4-(5-phenylimidazo[1,2-α]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyric acid (365 mg, yield 94%) as colorless crystals. m.p. 160-161° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-782db8e523a04a53a45c4f145d2bb486
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251926B1

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