Water → 5-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid

HRID 1047794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047794
C([O:3][C:4]([C:6]1([NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=2/[CH:25]=[CH:26]/[CH3:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[F:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1/[CH:25]=[CH:26]/[CH3:27])([C:4]([OH:5])=[O:3])[CH2:14]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593140805-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Produkt 1

HCID 251608005-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acidAusbeute 111,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The mixture 5-fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (153) (260 mg, 0.68 mmol) and KOH (600 mg, 10.7 mmol) is dissolved in EtOH (8 mL) and water (0.2 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 2.5 h. After concentration in vacuo, the residue is dissolved in water (30 mL) and acidified with conc. HCl until no more precipitate came out of the water. The filtered compound is purified by HPLC to give a pure product (154) as white solid (267 mg, 100%).

Aufarbeitung

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (30 mL)
  6. customThe filtered compound is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f4b9ba28423048b7b8841487ce5fe04c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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