Water → (S)-3-(tert-Butoxycarbonylamino)-1-(4-methoxy-5-isoquinolinesulfonyl)pyrrolidine

HRID 2425388ノート

反応式

HRID 2425388 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].O.[C:32](OCC)(=[O:34])C>CO.N1C=CC=CC=1.[Cu](I)I>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([O:34][CH3:32])=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 67242852(S)-3-(tert-Butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

生成物 1

HCID 67243480(S)-3-(tert-Butoxycarbonylamino)-1-(4-methoxy-5-isoquinolinesulfonyl)pyrrolidine

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 887Methanol溶媒2 回HCID 1049Pyridine溶媒

実験手順

A solution of Intermediate 1a (337 mg) obtained in Example 1-1, Step A in methanol (2.7 ml) and pyridine (2.7 ml) was added with a solution of 28% sodium methylate (847 mg) in methanol, and then with copper iodide (70 mg), and the mixture was stirred at 65° C. for 30 hours. The reaction mixture was cooled to room temperature, and added with water (30 ml) and ethyl acetate (30 ml), and the insoluble solids were removed by filtration through Celite. The organic layer of the filtrate was separated, and the aqueous layer was extracted 3 times with ethyl acetate (20 ml for each time). The combined organic layer was washed 3 times with saturated brine (30 ml for each time), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:methanol=30:1) to obtain the title compound (98 mg).

後処理

  1. customthe insoluble solids were removed by filtration through Celite
  2. customThe organic layer of the filtrate was separated
  3. extractionthe aqueous layer was extracted 3 times with ethyl acetate (20 ml for each time)
  4. washThe combined organic layer was washed 3 times with saturated brine (30 ml for each time), and
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (chloroform:methanol=30:1)

出典と根拠

ORDレコード
ord-c8efa55e53dd4f8097978b5c12731a96
出典データセット
uspto-grants-2011_06
特許番号
US07964613B2

反応ノート

読み込み中…