Sodium Sulfite → HCID 178451935, 화합물

HRID 538731노트

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HRID 538731 반응식
[I:1][C:2]1[N:3]=[C:4]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:5][C:6]=1I.[O-]S([O-])=O.[Na+].[Na+]>CCO.O>[I:1][C:2]1[N:3]=[C:4]([C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 24437Sodium SulfiteHCID 59449990(S)-tert-butyl 2-(4,5-diiodo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylate

생성물 1

HCID 178451935HCID 178451935, 화합물수율 80%

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

To a suspension of (S)-tert-butyl 2-(4,5-diiodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (6) (18.0 g, 36.8 mmol) in 800 mL EtOH/H2O (v/v=30:70) solution was added Na2SO3 (39.4 g, 312.9 mmol). The mixture was refluxed for 17 h. EtOH was evaporated under reduced pressure and the residue was diluted with EtOAc. The organic layer was washed with brine and dried over Na2SO4 and then concentrated to dryness. The residue was purified by silica gel column chromatography (PE/EtOAc=3:1 (v/v)) to afford (S)-tert-butyl 2-(4-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (7), (10.5 g, 80% yield) as a white solid. 1H NMR (500 MHz, DMSO) δ 1.16 (s, 5H), 1.38 (s, 4H), 1.80-1.91 (m, 3H), 2.08-2.18 (m, 1H), 3.30-3.46 (m, 2H), 4.66-4.76 (m, 1H), 7.16 (d, 1H, J=14 Hz), 12.04-12.09 (m, 1H) ppm; LC-MS (ESI): m/z calcd 364.0 (M+H)+.

후처리

  1. temperatureThe mixture was refluxed for 17 h
  2. customEtOH was evaporated under reduced pressure
  3. additionthe residue was diluted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by silica gel column chromatography (PE/EtOAc=3:1 (v/v))

출처 및 근거

ORD 기록
ord-0d5130a928a1452ab608fb1c3338439f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865756B2

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