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

HRID 528733노트

반응식

HRID 528733 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 26030Gold trichloride촉매HCID 6342Acetonitrile용매

반응 조건

온도
45 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc323ced19044b15a7803e5b9ebfcdbf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346816B2

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