Tetrabutylammonium Fluoride Trihydrate → 5-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one

HRID 1925503노트

반응식

HRID 1925503 반응식
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[C:39]5[C:34]=4[CH:35]=[CH:36][C:37](=[O:51])[NH:38]5)[O:25][Si](C(C)(C)C)(C)C)[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[C:39]5[C:34]=4[CH:35]=[CH:36][C:37](=[O:51])[NH:38]5)[OH:25])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

4

반응물 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 675208935-((1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-8-(benzyloxy)quinolin-2(1H)-one

생성물 1

HCID 675206375-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

To a solution of Intermediate 32 (0.48 g, 0.68 mmol) in tetrahydrofuran (12 mL) was added tetrabutylammonium fluoride trihydrate (0.284 g, 1.09 mmol). The reaction mixture was stirred at 45° C. for 3.5 hours. 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 to give the title compound as a yellow solid (0.375 g, 88%). MS (M+): 593.

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

출처 및 근거

ORD 기록
ord-a23753e32f414c7b91506d663dbea864
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178679B2

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