Potassium Carbonate → 2-(1-(5-Bromo-2-nitrophenyl)-4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid

HRID 1035270

반응식

HRID 1035270 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH:27]([CH2:31][C:32]([OH:34])=[O:33])[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N:28]2[CH2:29][CH2:30][N:25]([C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[CH2:26][CH:27]2[CH2:31][C:32]([OH:34])=[O:33])[CH:3]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 446077242-(4-(tert-Butoxycarbonyl)piperazin-2-yl)acetic acid

생성물 1

HCID 672481792-(1-(5-Bromo-2-nitrophenyl)-4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

4-Bromo-2-fluoro-1-nitrobenzene (5.3 g, 24.1 mmol) was dissolved in acetonitrile (70 mL) and water (10 mL). To this mixture, potassium carbonate (10 g, 72.3 mmol) and 2-(4-(tert-butoxycarbonyl)piperazin-2-yl)acetic acid (7.1 g, 28.9 mmol) were added. The resulting mixture was heated at 70° C. for 2 days. The mixture thus obtained was concentrated and ethyl acetate was added. 1 N HCl was then added slowly to the reaction solution until pH=6. The water layer was separated and washed multiple times with ethyl acetate. The organic layers thus obtained were combined and concentrated. The crude material thus obtained was purified by silica gel chromatography eluting with a gradient of 0% to 10% of methanol in dichloromethane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.28 (br s), 7.71-7.83 (m, 1H), 7.56-7.66 (m, 1H), 7.30-7.40 (m, 1H), 3.56-3.82 (m, 3H), 3.33-3.44 (m, 1H), 2.99-3.24 (m, 2H), 2.87 (m, 1H), 2.32-2.47 (m, 1H), 2.17-2.29 (m, 1H), 1.32-1.51 (s, 9H); MS (DCI+) m/z 444.1 (M+H)+.

후처리

  1. customThe mixture thus obtained
  2. concentrationwas concentrated
  3. additionethyl acetate was added
  4. addition1 N HCl was then added slowly to the reaction solution until pH=6
  5. customThe water layer was separated
  6. washwashed multiple times with ethyl acetate
  7. customThe organic layers thus obtained
  8. concentrationconcentrated
  9. customThe crude material thus obtained
  10. customwas purified by silica gel chromatography
  11. washeluting with a gradient of 0% to 10% of methanol in dichloromethane

출처 및 근거

ORD 기록
ord-53c9427b942044f38f12349787042f79
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546377B2

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