Sodium Hydroxide → Benzoic Acid

HRID 2220376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220376
C(OC(N(C[C@H](O)C1C=CC=CC=1)CCC1C=CC([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[C:19](C3SC=CC=3)[CH:18]=2)=CC=1)=O)(C)(C)C.[OH-].[Na+]>CO>[C:23]([OH:25])(=[O:24])[C:20]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 69103883HCID 69103883, Verbindung

Produkt 1

HCID 243Benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of methyl 4′-[2-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(2-thienyl)-4-bipheylcarboxylate (188 mg) in methanol (3.3 ml) was added 1N aqueous sodium hydroxide solution (1.0 ml), and the mixture was stirred at 40° C. for 3 hours. The solvent was removed by evaporation, and the aqueous solution was acidified with 1N aqueous hydrochloride solution and extracted with ethyl acetate (30 ml×2). The combined organic layers were washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give a benzoic acid product. To a solution of the product in ethyl acetate (1.0 ml) was added 4N hydrogen chloride in ethyl acetate (1.0 ml), and the mixture was stirred at room temperature for 12 hours. The resultant solid was collected by filtration and dried to give 4′-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(2-thienyl)-4-biphenylcarboxylic acid hydrochloride (139 mg).

Aufarbeitung

  1. customThe solvent was removed by evaporation
  2. extractionextracted with ethyl acetate (30 ml×2)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e7800ecd06ee4df1be433138b8291580
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417060B2

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