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 1925528ノート

反応式

HRID 1925528 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7d7248ee4a894d248bb6c9eb2bfdfa4a
出典データセット
uspto-grants-2012_05
特許番号
US08178679B2

反応ノート

読み込み中…