Ethanol → 5-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047795
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1/[CH:23]=[CH:24]/[CH3:25])([C:11]([OH:13])=[O:12])[CH2:5]2.[CH3:27]CO>[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:14][C:15](=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[CH2:23][CH:24]([CH3:27])[CH3:25])([C:11]([OH:13])=[O:12])[CH2:5]2

Komponenten

4

Edukt 2

HCID 702EthanolHCID 251608005-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid

Produkt 1

HCID 251606695-Fluoro-2-(2-isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

5-Fluoro-2-[3-methyl-2-((E)-propenyl)-benzoylamino]-indan-2-carboxylic acid (154) (270 mg, 0.76 mmol) is dissolved in absolute EtOH (15 mL) by heating. The resulting solution is cooled down to RT under argon and then is added the catalyst, Pd—C (5 wt. % Pd, 125 mg, 5.9% mmol). The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, 50° C., overnight. The catalyst is removed by filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (155) as white solid (210 mg, 78%).

Aufarbeitung

  1. temperatureby heating
  2. customThe resulting reaction mixture
  3. custom50 psi, 50° C., overnight
  4. customThe catalyst is removed by filtration through a pre-column (10 g silica gel)
  5. washwashed with EtOH
  6. concentrationThe combined organic solution is concentrated in vacuo
  7. customThe residue is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-81549fef3bc04928a16d129eaefd0dfb
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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