Oxazolo(4,5-b)pyridine → (S)-[1-(hydroxy-oxazolo[4,5-b]pyridin-2-yl-methyl)-propyl]-carbamic acid tert-butyl ester

HRID 1444567

Reaktionsgleichung

Reaktionsgleichung von HRID 1444567
[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][CH3:27])[CH:24]=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:26][CH3:27])[CH: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

5

Edukt 3

HCID 10103159Oxazolo(4,5-b)pyridineHCID 10241556tert-butyl N-((2S)-1-oxobutan-2-yl)carbamateHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 21048468(S)-[1-(hydroxy-oxazolo[4,5-b]pyridin-2-yl-methyl)-propyl]-carbamic acid tert-butyl esterAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a round bottom flask equipped with stir bar was placed oxazolo[4,5-b]pyridine (600 mg, 5 mmol) in THF (30 mL) and the reaction mixture was cooled to 0° C. under N2 atomosphere. Isopropylmagnesium chloride (2 M 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 THF (20 mL) 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

  1. customIn a round bottom flask equipped
  2. stirringAfter stirring for 1 h at 0° C.
  3. customThe ice bath was removed
  4. temperatureto warm to room temperature
  5. customthe reaction mixture was quenched with saturated ammonium chloride solution
  6. concentrationconcentrated to dryness
  7. extractionThe residue was extracted with EtOAc
  8. washwashed with brine
  9. customdried with anhyd
  10. filtrationMgSO4, filtered
  11. concentrationconcentrated
  12. customThe crude product was purified by chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-85d2cd5aeb51416fb3424512673da6a8
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662849B2

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