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

HRID 528733ノート

反応式

HRID 528733 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 26030Gold trichloride触媒HCID 6342Acetonitrile溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bc323ced19044b15a7803e5b9ebfcdbf
出典データセット
uspto-grants-2016_05
特許番号
US09346816B2

反応ノート

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