Sodium Sulfite → HCID 178451935、化合物

HRID 538731ノート

反応式

HRID 538731 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 178451935HCID 178451935、化合物収率 80%

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

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)+.

後処理

  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))

出典と根拠

ORDレコード
ord-0d5130a928a1452ab608fb1c3338439f
出典データセット
uspto-grants-2014_10
特許番号
US08865756B2

反応ノート

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