Pyridine → Methyl {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

HRID 602654노트

반응식

HRID 602654 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[N:9]2[CH2:12][C:11]([CH:14]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=3)[C:15]([O:17][CH3:18])=[O:16])(O)[CH2:10]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>ClCCl>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]2[CH2:10][C:11](=[C:14]([C:19]3[CH:20]=[C:21]([F:26])[CH:22]=[C:23]([F:25])[CH:24]=3)[C:15]([O:17][CH3:18])=[O:16])[CH2:12]2)=[CH:32][CH:31]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 57346892DiazabicycloundecaneHCID 67055297Methyl{1-[bis(4-chlorophenyl)methyl]-3-hydroxyazetidin-3-yl}(3,5-difluorophenyl)acetate

생성물 1

HCID 57559907Methyl {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 0.71 g (1.44 mmol) of methyl {1-[bis(4-chlorophenyl)methyl]-3-hydroxyazetidin-3-yl}(3,5-difluorophenyl)acetate, 0.295 g (1.73 mmol) of methanesulfonyl anhydride, and 0.400 mL pyridine in 5 mL of dichloromethane was stirred at room temperature overnight. To this was added 0.400 mL of diazabicycloundecane and the solution remained stirring at room temperature. The mixture was partitioned between ether and water and the aqueous layer was washed with 20 mL of ether. The organic layers were washed with brine, combined, dried over MgSO4 and concentrated. The residue was filtered through a pad of silica gel using 20% ether-hexane to afford the title compound; 1NMR (CDCl3) δ 3.67 (s, 3H), 3.84 (m, 2H), 4.25 (m, 2H), 4.54 (s, 1H), 6.76 (m, 1H), 6.78 (m, 2H), 7.33 (m, 4H), 7.38 (m, 4H); Mass Spectrum: m/e=474 (M+1 35Cl, 35Cl) and 476 (M+1 35Cl, 37Cl).

후처리

  1. customThe mixture was partitioned between ether and water
  2. washthe aqueous layer was washed with 20 mL of ether
  3. washThe organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. filtrationThe residue was filtered through a pad of silica gel using 20% ether-hexane

출처 및 근거

ORD 기록
ord-cb5e022a02c6433ba644013edf6b463d
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906503B2

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