Sodium hydride → HCID 178448628、化合物

HRID 340648

反応式

HRID 340648 の反応式
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].[CH2:10]([N:14]1[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:17]=2[S:16]/[C:15]/1=[N:23]\[C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1F)[CH2:11][CH2:12][CH3:13]>C1COCC1>[CH2:10]([N:14]1[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][C:17]=2[S:16]/[C:15]/1=[N:23]\[C:24](=[O:36])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[O:5][CH2:4][CH2:3][C:2]([OH:7])([CH3:6])[CH3:1])[CH2:11][CH2:12][CH3:13]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 247470IsopentyldiolHCID 178448621HCID 178448621、化合物

生成物 1

HCID 178448628HCID 178448628、化合物収率 90.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
2.5 °C

実験手順

3-Methylbutane-1,3-diol (42 mg, 0.4 mmol) in THF (1 mL) was treated with NaH (60%) (16 mg, 0.4 mmol) at room temperature for 20 min. To the above mixture, which was cooled to 0-5° C., was added the product from Example 20B (80 mg, 0.2 mmol) in THF (1 mL). After 20 min. the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford 87 mg (90%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.04 (t, J=7.32 Hz, 3H) 1.36 (s, 6H) 1.47-1.55 (m, 2H) 1.88-1.96 (m, 2H) 2.13 (t, J=5.80 Hz, 2H) 4.35 (t, J=5.80 Hz, 2H) 4.54 (t, J=7.63 Hz, 2H) 5.12 (brs, 1H) 7.11 (d, J=8.54 Hz, 1H) 7.61 (d, J=5.19 Hz, 1H) 7.74 (dd, J=8.54, 2.14 Hz, 1H) 8.49 (d, J=5.19 Hz, 1H) 8.68 (s, 1H) 8.72 (s, 1H); MS (ESI+) m/z 482 (M+H)+.

後処理

  1. customAfter 20 min. the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-4fbaf80223a743fe9d8a03d24f29aea6
出典データセット
uspto-grants-2014_11
特許番号
US08895592B2

関連ノート

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