Sodium Hydroxide → HCID 58978946, Verbindung

HRID 1181075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181075
[C:1]([O:5][C:6](=[O:39])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][N:31](C)[C:32](=O)C(F)(F)F)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6](=[O:39])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][NH:31][CH3:32])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 589793073-(4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-2-{[methyl-(2,2,2-trifluoro-acetyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester

Produkt 1

HCID 58978946HCID 58978946, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A solution of 3-(4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-2-{[methyl-(2,2,2-trifluoro-acetyl)-amino]-methyl}-phenyl)-propionic acid tert-butyl ester (111 mg, 0.20 mmol) in methanol (5 mL) and THF (5 mL) was treated with 2N NaOH (1.0 mL, 2.0 mmol) and heated at 55° C. for 1 h. The reaction mixture was cooled, concentrated, neutralized with 1N HCl and extracted into EtOAc. The organic layer was washed with saturated NaHCO3 solution and brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel radial chromatography (CH2Cl2/methanol 95/5 to 90/10) to the title compound (37 mg, 42%). MS (ES) m/z 451.3 [M+1].

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. extractionextracted into EtOAc
  4. washThe organic layer was washed with saturated NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel radial chromatography (CH2Cl2/methanol 95/5 to 90/10) to the title compound (37 mg, 42%)

Quellen und Nachweise

ORD-Eintrag
ord-462e3706aef14b65961e68aabd13575a
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282501B2

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