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Water → 2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one

HRID 1736214
ノート
印刷プレビュー

反応式

HRID 1736214 の反応式
[NH2:1][C:2]1[C:7]2[C:8](=[O:30])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][O:20][CH3:21])=[C:14]([F:29])[CH:13]=3)[O:11][C:6]=2[C:5]([F:31])=[CH:4][C:3]=1[F:32].[H-].[Na+].Br[CH2:36][CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40].O>CN(C)C=O>[C:25]([O:24][C:22]([N:18]([C:15]1[CH:16]=[CH:17][C:12]([C:10]2[O:11][C:6]3[C:5]([F:31])=[CH:4][C:3]([F:32])=[C:2]([NH:1][CH2:36][CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40])[C:7]=3[C:8](=[O:30])[CH:9]=2)=[CH:13][C:14]=1[F:29])[CH2:19][O:20][CH3:21])=[O:23])([CH3:27])([CH3:28])[CH3:26]
参加物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 24758Sodium hydrideHCID 1375215-Bromo-2-methyl-2-penteneHCID 194347945-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-one

生成物 1

HCID 194348222-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one収率 38%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2.70 g (6.00 mmol) of the above 5-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-4H-1-benzopyran-4-one was dissolved in 60 mL of dimethylformamide under argon atmosphere, 480 mg (12.0 mmol) of sodium hydride (60% oil dispersion) and 4.0 mL (30 mmol) of 5-bromo-2-methyl-2-pentene were added under ice-cooling and the mixture was stirred at room temperature for 18 hours. The reaction solution was cooled on ice, water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed twice with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:acetonitrile=30:1) to give 1.21 g of 2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl]-6,8-difluoro-5-(4-methyl-3-pentenylamino)-4H-1-benzopyran-4-one (yield: 38%).

後処理

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic layer was washed twice with water and once with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:acetonitrile=30:1)

出典と根拠

ORDレコード
ord-0f3834f2211e4c9288cc60c83e5f763c
出典データセット
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05539112

反応ノート

読み込み中…

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