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

HRID 528733Notes

Reaction equation

HRID 528733 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 26030Gold trichlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bc323ced19044b15a7803e5b9ebfcdbf
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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