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

HRID 1736213
ノート
印刷プレビュー

反応式

HRID 1736213 の反応式
[NH2:1][C:2]1[C:7]2[C:8](=[O:27])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:14]([F:26])[CH:13]=3)[O:11][C:6]=2[C:5]([F:28])=[CH:4][C:3]=1[F:29].[H-].[Na+].[CH3:32][O:33][CH2:34]Cl.O>CN(C)C=O>[NH2:1][C:2]1[C:7]2[C:8](=[O:27])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:32][O:33][CH3:34])=[C:14]([F:26])[CH:13]=3)[O:11][C:6]=2[C:5]([F:28])=[CH:4][C:3]=1[F:29]
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 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 19434972HCID 19434972、化合物

生成物 1

HCID 194347945-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-one収率 92.3%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

2.41 g (5.94 mmol) of Compound 51 obtained in Example 51 was dissolved in 60 mL of dimethylformamide under argon atmosphere, 237 mg (5.94 mmol) of sodium hydride (60% oil dispersion) and 0.47 mL (6.24mmol) of chloromethyl methyl ether were added under ice-cooling and the mixture was stirred at room temperature for 40 minutes. The reaction solution was cooled on ice, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed once 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:l) to give 2.47 g of 5-amino-2-[4-[N-(tert-butoxycarbonyl)-N-methoxymethylamino]-3-fluorophenyl)-6,8-difluoro-4H-1-benzopyran-4-one (yield: 92%).

後処理

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed once 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:l)

出典と根拠

ORDレコード
ord-c0e8acb201bd4856b7cb9f8981df71ef
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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