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Water → (5R)-5-[(E)-2-[4-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-3-methylphenyl]-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

HRID 70623
ノート
印刷プレビュー

反応式

HRID 70623 の反応式
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl:19][C:20]1[CH:21]=[CH:22][C:23](/[C:28](/[C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH3:43])[CH:37]=2)=[CH:29]/[C@@H:30]2[NH:34][C:33](=[O:35])[CH2:32][CH2:31]2)=[N:24][C:25]=1[O:26][CH3:27].O>CN(C)C=O>[Si:12]([O:11][CH2:10][CH2:9][CH2:8][O:42][C:39]1[CH:40]=[CH:41][C:36](/[C:28](/[C:23]2[CH:22]=[CH:21][C:20]([Cl:19])=[C:25]([O:26][CH3:27])[N:24]=2)=[CH:29]\[C@@H:30]2[NH:34][C:33](=[O:35])[CH2:32][CH2:31]2)=[CH:37][C:38]=1[CH3:43])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 67398764(5R)-5-[(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-(4-hydroxy-3-methylphenyl)ethenyl]pyrrolidin-2-one

生成物 1

HCID 67396325(5R)-5-[(E)-2-[4-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-3-methylphenyl]-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

Potassium carbonate (470 mg) and (3-bromopropoxy)-tert-butyldimethylsilane (600 μL) were sequentially added to a solution of (5R)-5-[(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-(4-hydroxy-3-methylphenyl)ethenyl]pyrrolidin-2-one obtained in Example 4-50(2) (610 mg) in N,N-dimethylformamide (10 mL), and the mixture was stirred at room temperature for 15 hours and at 65° C. for three hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:4→2:8) to give (5R)-5-[(E)-2-[4-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-3-methylphenyl]-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a colorless amorphous (879 mg, 97%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:4→2:8)

出典と根拠

ORDレコード
ord-f2fd243476544d9fba6c9ca993d151fa
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート