Tetrabutylammonium Fluoride → 8-(benzyloxy)-5-(1-(hydroxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one

HRID 1925528노트

반응식

HRID 1925528 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([O:46][Si](C(C)(C)C)(C)C)[CH2:21][NH:22][C:23]([CH3:45])([CH3:44])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][C:34]34[CH2:43][CH:38]5[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]5)[CH2:35]3)[CH2:41]4)[CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:46])[CH2:21][NH:22][C:23]([CH3:44])([CH3:45])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][C:34]34[CH2:43][CH:38]5[CH2:37][CH:36]([CH2:42][CH:40]([CH2:39]5)[CH2:41]3)[CH2:35]4)[CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 675205018-(benzyloxy)-5-(1-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one

생성물 1

HCID 675205378-(benzyloxy)-5-(1-(hydroxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Intermediate 88 (0.748 g, 1.02 mmol) in tetrahydrofuran (15 mL) were added 0.546 g (1.73 mmol) of tetrabutylammonium fluoride. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and water. The organic layer was washed several times with water and the solvent was removed under reduced pressure. The crude was purified by column chromatography with silica gel, eluting with dichloromethane/methanol 90:4 to give 0.505 g (80% yield) of the title compound.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was partitioned between ethyl acetate and water
  3. washThe organic layer was washed several times with water
  4. customthe solvent was removed under reduced pressure
  5. customThe crude was purified by column chromatography with silica gel
  6. washeluting with dichloromethane/methanol 90:4

출처 및 근거

ORD 기록
ord-7d7248ee4a894d248bb6c9eb2bfdfa4a
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178679B2

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