Ethyl Acetate → tert-butyl ((2S)-1-((2-(4-(benzyloxy)phenyl) [1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamate

HRID 2277248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277248
[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][C:12]([C:13]([NH:15][C:16]2[C:17](Cl)=[CH:18][C:19]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])=[N:20][CH:21]=2)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.[Cu]I>[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][C:12]([C:13]2[O:14][C:17]3[CH:18]=[C:19]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])[N:20]=[CH:21][C:16]=3[N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86731322tert-butyl ((2S)-1-((5-((4-(benzyloxy)benzoyl)amino)-4-chloropyridin-2-yl)oxy)propan-2-yl)carbamate

Produkt 1

HCID 86731321tert-butyl ((2S)-1-((2-(4-(benzyloxy)phenyl) [1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamateAusbeute 35,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A suspension of tert-butyl ((2S)-1-((5-((4-(benzyloxy)benzoyl)amino)-4-chloropyridin-2-yl)oxy)propan-2-yl)carbamate (2.50 g), potassium carbonate (1.35 g) and copper(I) iodide (93.9 mg) in DMF (20 mL) was stirred at 160° C. for 3.5 hr. The reaction mixture was subjected to silica gel chromatography (NH, ethyl acetate), washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the obtained solid was washed with ethyl acetate/hexane to give the title compound (830 mg).

Aufarbeitung

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washthe obtained solid was washed with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ce181cad8c294b9ba999ee9c450d9795
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133129B2

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