2-(Bromomethyl)tetrahydro-2H-pyran → N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(tetrahydro-pyran-2-ylmethylsulfanyl)-propionamide

HRID 73240노트

반응식

HRID 73240 반응식
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C:13]([S:16][C:17](=O)[CH3:18])([CH3:15])[CH3:14])=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].BrC[CH:22]1[CH2:27][CH2:26][CH2:25]C[O:23]1.C[O-].[Na+]>C(O)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:12])[C:13]([CH3:15])([S:16][CH2:17][CH:18]2[CH2:25][CH2:26][CH2:27][CH2:22][O:23]2)[CH3:14])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 10942334Sodium MethoxideHCID 59703935thioacetic acid S-[1-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-1-methyl-ethyl]ester

생성물 1

HCID 59703962N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(tetrahydro-pyran-2-ylmethylsulfanyl)-propionamide수율 99.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
130 °C

실험 절차

To a solution of 100 mg (0.352 mmol) of thioacetic acid S-[1-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-1-methyl-ethyl]ester (synthesized according to Method F, step 1) in ethanol (2 mL) were added 126 mg (0.704 mmol) of 2-(bromomethyl)tetrahydropyran and 76 mg (1.41 mmol) of sodium methoxide at room temperature. The reaction was heated to 130° C. for 0.5 h within a microwave (CEM Discover). The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (5 ml) and washed with saturated aqueous NaHCO3 solution (5 ml). The organic phase was dried (Na2SO4), filtered and concentrated under reduced pressure to yield 119 mg of N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-2-(tetrahydro-pyran-2-ylmethylsulfanyl)-propionamide.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (5 ml)
  3. washwashed with saturated aqueous NaHCO3 solution (5 ml)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6e277728e3314baaa272050fa03f27eb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829034B2

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