1-Boc-N-(2-propyn-1-yl)azetidine-3-carboxamide → 2-(1-Boc-3-azetidinyl)-5-methyloxazole

HRID 528733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528733
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12](=[O:17])[NH:13][CH2:14][C:15]#[CH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(#N)C.[Au](Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]2[O:17][C:15]([CH3:16])=[CH:14][N:13]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 866671721-Boc-N-(2-propyn-1-yl)azetidine-3-carboxamide

Produkt 1

HCID 679793952-(1-Boc-3-azetidinyl)-5-methyloxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 26030Gold trichlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To 0.22 g (0.92 mmol) 3-prop-2-ynylcarbamoyl-azetidine-1-carboxylic acid tert-butyl ester in 4 mL anhydrous acetonitrile, under nitrogen, was added 14 mg (0.046 mmol) gold (III) chloride and the reaction mixture was stirred at 45° C. for 6 hours. After evaporation of the solvent, 20 mL DCM was added, the organic layer was washed with H2O (2×10 mL) then dried over Na2SO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 6:4 to 5:5), and used for the next step without further purification.

Aufarbeitung

  1. customAfter evaporation of the solvent, 20 mL DCM
  2. additionwas added
  3. washthe organic layer was washed with H2O (2×10 mL)
  4. dry with materialthen dried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent the product
  6. customwas purified by column chromatography (silica, heptane/EtOAc 6:4 to 5:5)
  7. customused for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-bc323ced19044b15a7803e5b9ebfcdbf
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346816B2

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