Tetrahydrofuran → 4-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid

HRID 1616623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616623
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][C:7]1[O:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[N:11]=1.C1COCC1.[OH-].[Na+]>CCO>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[N:11]=[C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:19])=[O:2])[O:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 591677464-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid methyl ester

Produkt 1

HCID 597990014-[4-(2-Amino-phenyl)-oxazol-2-yl]-butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Combine 4-[4-(2-amino-phenyl)-oxazol-2-yl]-butyric acid methyl ester (2.36 g, 9.1 mmol) with THF (3 mL), EtOH (3 mL) and 2N NaOH (20 mL) and stir until hydrolysis is complete. Concentrate the mixture, dilute the residue with water and adjust the pH to 3.5-4.0 with aq HCl. Extract the mixture with EtOAc and dry the extracts over Na2SO4 before concentrating. Chromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for recovery of 4-[4-(2-amino-phenyl)-oxazol-2-yl]-butyric acid (1.63 g, 73%). MS (ES): (M+1)+ 247.1 m/z.

Aufarbeitung

  1. concentrationConcentrate the mixture
  2. additiondilute the residue with water
  3. extractionExtract the mixture with EtOAc
  4. dry with materialdry the extracts over Na2SO4
  5. concentrationbefore concentrating

Quellen und Nachweise

ORD-Eintrag
ord-aeb00cc70bc64fbfa07874dd716ddd4c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765796B2

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