Water → N-{4-[4-formyl-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide

HRID 2402054ノート

反応式

HRID 2402054 の反応式
[CH3:1][Si:2]([CH3:30])([CH3:29])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]1[S:16][C:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=2)=[N:14][C:13]=1[CH:27]=C.O.I([O-])(=O)(=O)=[O:33].[Na+]>O1CCCC1.[Os](=O)(=O)(=O)=O.O>[CH:27]([C:13]1[N:14]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:26])[CH3:25])[CH:18]=2)[S:16][C:12]=1[C:8]1[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:29])[CH3:30])[CH:11]=[CH:10][N:9]=1)=[O:33]

参加物

7

反応物 3

HCID 962WaterHCID 23667635Sodium periodateHCID 68006825N-{4-[5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-4-vinyl-1,3-thiazol-2-yl]pyridin-2-yl}acetamide

生成物 1

HCID 86667476N-{4-[4-formyl-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-1,3-thiazol-2-yl]pyridin-2-yl}acetamide収率 38.3%

試薬・触媒・溶媒 3

HCID 962Water触媒HCID 30318Osmium Tetroxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-{4-[5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-4-vinyl-1,3-thiazol-2-yl]pyridin-2-yl}acetamide (0.650 g, 1.47 mmol) was dissolved in tetrahydrofuran (20 mL) and water (10 mL) at ambient temperature and 0.157 M osmium tetraoxide in water (93 uL, 0.014 mmol) was added. The mixture was stirred at room temperature for 5 minutes. Sodium metaperiodate (0.661 g, 3.09 mmol) was then added in portions over 20 minutes and the mixture was stirred at room temperature overnight. Solids were removed by filtration and washed with THF (2×50 mL) and ethyl acetate (2×5 mL). The filtrate was extracted with ethyl acetate (3×100 mL). The extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Crude material was purified by silica gel chromatography (0 to 30% ethyl acetate in hexanes) to afford the title compound (0.25 g, 38%). LCMS: (FA) ES+, 444. 1H NMR (400 MHz, CDCl3) δ: 8.75 (s, 1H), 10.21 (s, 1H), 8.41 (d, J=5.18 Hz, 1H), 8.20-8.07 (m, 1H), 7.76 (dd, J=5.21, 1.58 Hz, 1H), 7.30 (dd, J=2.87, 1.21 Hz, 2H), 5.32 (s, 2H), 3.50-3.33 (m, 2H), 2.26 (s, 3H), 0.93-0.78 (m, 2H), −0.04 (s, 9H).

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. customSolids were removed by filtration
  3. washwashed with THF (2×50 mL) and ethyl acetate (2×5 mL)
  4. extractionThe filtrate was extracted with ethyl acetate (3×100 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customCrude material was purified by silica gel chromatography (0 to 30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-bf2573222de04543ba04b7661a5d292e
出典データセット
uspto-grants-2014_08
特許番号
US08796271B2

反応ノート

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