Sodium Hydroxide → tert-Butyl 4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)methyl]piperazine-1-carboxylate

HRID 906426노트

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HRID 906426 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7](S(C1C=CC=CC=1)(=O)=O)[CH:6]=[C:5]2[CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1.[OH-].[Na+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[CH2:22][N:23]1[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67390586tert-Butyl 4-{[6-bromo-1-oxo-2-(phenylsulfonyl)-1,2-dihydroisoquinolin-4-yl]methyl}piperazine-1-carboxylate

생성물 1

HCID 67390749tert-Butyl 4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)methyl]piperazine-1-carboxylate수율 28.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 4-{[6-bromo-1-oxo-2-(phenylsulfonyl)-1,2-dihydroisoquinolin-4-yl]methyl}piperazine-1-carboxylate (Example 27a, 1.35 g) in THF (10 mL) was added sodium hydroxide (0.29 g) in water (5 mL). The reaction was stirred at room temperature for 2 h. The reaction was then heated to 50° C. for 2 h. The volatiles were removed under reduced pressure, and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The aqueous was extracted further with ethyl acetate (2×100 mL), and the combined organics dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was triturated with ethyl acetate to afford the subtitle compound as a white solid (0.29 g).

후처리

  1. temperatureThe reaction was then heated to 50° C. for 2 h
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. extractionThe aqueous was extracted further with ethyl acetate (2×100 mL)
  5. dry with materialthe combined organics dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-c04853888d954a1886540ef580b70c1a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012980B2

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