18-Crown-6 → Methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-1-{4-[[di(tert-butoxy)phosphoryl](difluoro)methyl]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate

HRID 1371019노트

반응식

HRID 1371019 반응식
[C:1]([O:5][C:6](=[O:38])[C:7]([F:37])([F:36])[O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][CH:14]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)[C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1OCCOCCOCCOCCOCCOC1.CC(C)([O-])C.[K+].Br[CH2:64][C:65]1[CH:70]=[CH:69][C:68]([C:71]([P:74](=[O:85])([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])[O:75][C:76]([CH3:79])([CH3:78])[CH3:77])([F:73])[F:72])=[CH:67][CH:66]=1>C1COCC1>[C:1]([O:5][C:6](=[O:38])[C:7]([F:36])([F:37])[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]([C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=2)([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([C:71]([P:74]([O:80][C:81]([CH3:84])([CH3:83])[CH3:82])([O:75][C:76]([CH3:77])([CH3:79])[CH3:78])=[O:85])([F:72])[F:73])=[CH:67][CH:66]=2)[C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:16])=[CH:34][CH:35]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 2855718-Crown-6HCID 15922636Di(tert-butyl) [4-(bromomethyl)phenyl](difluoro)methylphosphonateHCID 18510241Methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 18510258Methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-1-{4-[[di(tert-butoxy)phosphoryl](difluoro)methyl]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate수율 48.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate (0.176 g, 0.333 mmol)) in degassed THF (1.7 ml), were added at −20° C. 18-crown-6 (0.15 g) and potassium tert-butoxide 1 M in THE (0.379 ml ). Di(tert-butyl) [4-(bromomethyl)phenyl](difluoro)methylphosphonate (0.156 g, 0.378 mmol) was then added and the reaction mixture was allowed to warm to room temperature. The reaction was quenched with saturated ammonium acetate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography using hexane/ethyl acetate 20% giving 0.140 g of the title compound.

후처리

  1. customThe reaction was quenched with saturated ammonium acetate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-a3c05e608267479fad71a001cb8aa16a
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583126B2

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