Sodium Iodide → HCID 59708792, 화합물

HRID 1097299노트

반응식

HRID 1097299 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:29][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34]Br)[CH3:28]>CC(C)=O>[CH2:27]([O:29][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][N:15]1[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:18])[CH2:13][CH2:14]1)[CH3:28]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 41346911-(4-Boc-aminobutyl)piperazine

생성물 1

HCID 59708792HCID 59708792, 화합물수율 56%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of (4-piperazin-1-yl-butyl)carbamic acid tert-butyl ester (17) (1.94 g, 7.54 mmol), sodium iodide (1.13 g, 7.54 mmol), potassium carbonate (3.13 g, 22.61 mmol), and 5-bromopentanoic acid ethyl ester (1.55 mL, 9.80 mmol) in acetone (60 mL) was stirred at reflux for 24 h. After removal of solvent by rotary evaporation, the resulting residue was diluted with dichloromethane and insoluble inorganics were filtered off. The liquid filtrate was concentrated in vacuo and the resulting residue was purified by Biotage silica gel column chromatography using methanol/dichloromethane (gradient 0% to 5%) to give a yellow oil, which was further purified by Biotage chromatography using ethyl acetate/dichloromethane (gradient 30% to 99%) to afford 18 as a yellow oil (1.62 g, 56%): 1H NMR (500 MHz, CDCl3) δ 1.27 (t, 3H), 1.43 (s, 9H), 1.52 (m, 6H), 1.65 (m, 2H), 2.34 (m, 6H), 2.48 (m, 6H), 3.11 (m, 2H), 4.12 (q, 2H), 5.21 (br, 1H); ESI MS m/z 386 [C20H39N3O4+H]+.

후처리

  1. temperatureat reflux for 24 h
  2. customAfter removal of solvent
  3. customby rotary evaporation
  4. additionthe resulting residue was diluted with dichloromethane and insoluble inorganics
  5. filtrationwere filtered off
  6. concentrationThe liquid filtrate was concentrated in vacuo
  7. customthe resulting residue was purified by Biotage silica gel column chromatography
  8. customto give a yellow oil, which
  9. customwas further purified by Biotage chromatography

출처 및 근거

ORD 기록
ord-f132e485dd4f4bdb8c4ad3331068733c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143256B2

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