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Sodium Hydroxide → 4-Methyl-2-[5-(2-propyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-pentanoic acid

HRID 889686
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 889686
C([O:3][C:4](=[O:35])[CH:5]([C:10]1[CH:11]=[C:12]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[CH:13]=[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH2:23][CH3:24])[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C.[OH-].[Na+]>CO>[CH3:9][CH:7]([CH3:8])[CH2:6][CH:5]([C:10]1[CH:11]=[C:12]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=2)[CH:13]=[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH2:23][CH3:24])[CH:15]=1)[C:4]([OH:35])=[O:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 576659754-Methyl-2-[5-(2-propyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-pentanoic acid ethyl ester

Produkt 1

HCID 252679794-Methyl-2-[5-(2-propyl-piperidin-1-yl)-4'-trifluoromethyl-biphenyl-3-yl]-pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-methyl-2-[5-(2-propyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-pentanoic acid ethyl ester (24 mg, 0.05 mmol) in MeOH (1 mL) was added 3N NaOH (0.200 mL) and heated to 60° C. for 2 h. The reaction was concentrated in vacuo to remove MeOH. The thick liquid was acidified to pH 2 by 2N HCl. The resulting acidic solution was extracted with EtOAc. The organic fraction was dried (MgSO4) and concentrated in vacuo. The crude mixture was purified by Gilson reverse phase column chromatography to obtain 4-methyl-2-[5-(2-propyl-piperidin-1-yl)-4′-trifluoromethyl-biphenyl-3-yl]-pentanoic acid.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. customto remove MeOH
  3. extractionThe resulting acidic solution was extracted with EtOAc
  4. dry with materialThe organic fraction was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by Gilson reverse phase column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7c018116987a4a129d76b87557480585
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08252935B2

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