Hydrochloric Acid → 3,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyr-amidophenoxy]phenylacetic acid

HRID 1269583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269583
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[C:15](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:14]=2)=[C:7]([Cl:30])[CH:6]=1.[Li+].[OH-].Cl>C1COCC1>[Cl:11][C:9]1[CH:10]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[CH:6]=[C:7]([Cl:30])[C:8]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[C:15](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:14]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18448782HCID 18448782, Verbindung

Produkt 1

HCID 102977453,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyr-amidophenoxy]phenylacetic acidAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl{3,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyramidophenoxy]phenyl}acetate(10 mg, 0.02 mmol), LiOH (2 mL, 1N) and THF (1 mL) was stirred at room temperature for 16 hours. The reaction mixture was poured into an aqueous solution of hydrochloric acid (1N). The aqueous layer was extracted with ethyl acetate, and the combined organic layers was washed with water, dried over MgSO4, filtered, and concentrated at reduced pressure to give 3.2 mg (35%) of 3,5-dichloro-4-[3-((E)-2-carboxyvinyl)-4-isobutyr-amidophenoxy]phenylacetic acid, m/z 452.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washthe combined organic layers was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6bd1486080c04a999e30edfbea4179be
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199265B2

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