Reaktionsgleichung
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.C([Mg]Cl)(C)C.[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:26]C)[CH:24]=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([NH:22][CH:23]([CH3:26])[C@@H:24]([C:2]1[O:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][CH:8]=2)[OH:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
In a clean roundbottom flask equipped with stir bar was placed oxazolo[4,5-b]pyridine (600 mg, 5 mmol) in 30 mL THF and the reaction mixture was cooled to 0° C. under N2 atmosphere. Isopropylmagnesium chloride (2M in THF, 2.5 ml, 5 mmol ) was added. After stirring for 1 h at 0° C., (S)-2-(tert-butoxycarbonyl)aminobutyraldehyde (573 mg, 3 mmol) in 20 ml THF was added. The ice bath was removed and the reaction mixture was allowed to warm to room temperature. After 2 h, the reaction mixture was quenched with saturated ammonium chloride solution and concentrated to dryness. The residue was extracted with EtOAc, then washed with brine, dried with anhyd. MgSO4, filtered and concentrated. The crude product was purified by chromatograph to yield 383 mg of the desired compound.
Aufarbeitung
- customIn a clean roundbottom flask equipped
- stirringAfter stirring for 1 h at 0° C.
- customThe ice bath was removed
- temperatureto warm to room temperature
- customthe reaction mixture was quenched with saturated ammonium chloride solution
- concentrationconcentrated to dryness
- extractionThe residue was extracted with EtOAc
- washwashed with brine
- customdried with anhyd
- filtrationMgSO4, filtered
- concentrationconcentrated
- customThe crude product was purified by chromatograph
Quellen und Nachweise
- ORD-Eintrag
- ord-0f7f3745dfef454bbb9619689f26fde3
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07091360B2
Verknüpfte Notizen
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