2-Pyridinesulfonic acid → 1-(Diphenylmethyl)azetidin-3-one

HRID 1437233

반응식

HRID 1437233 반응식
N1C=CC=CC=1S(O)(=O)=O.[CH:11]([N:24]1[CH2:27][CH:26]([OH:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CS(C)=O.C(N(CC)CC)C>[CH:11]([N:24]1[CH2:27][C:26](=[O:28])[CH2:25]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 2

HCID 948492-Pyridinesulfonic acidHCID 3304481-(Diphenylmethyl)azetidin-3-ol

생성물 1

HCID 37355581-(Diphenylmethyl)azetidin-3-one수율 60%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8471Triethylamine용매

실험 절차

Under cooling with ice, pyridinesulfonic acid (19.7 g) in dimethyl sulfoxide (84 mL) was added dropwise to 1-benzhydrylazetidin-3-ol (4.79 g) in triethylamine (27.9 mL), and the resultant mixture was stirred at 50° C. for 40 minutes. The reaction mixture was partitioned between ice-water and ethyl acetate. The organic layer was washed with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as a solid (2.85 g, 60%).

후처리

  1. customThe reaction mixture was partitioned between ice-water and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydrate
  4. filtrationfollowed by filtration
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-84f5b0b21cc84cbdb8c31f0d43e7a4d2
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622471B2

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