Sodium hydride → HCID 178448630、化合物

HRID 340649

反応式

HRID 340649 の反応式
[CH3:1][C:2]([OH:6])([CH3:5])[CH2:3][OH:4].[H-].[Na+].[CH2:9]([N:13]1[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:16]=2[S:15]/[C:14]/1=[N:22]\[C:23](=[O:35])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1F)[CH2:10][CH2:11][CH3:12]>C1COCC1>[CH2:9]([N:13]1[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:16]=2[S:15]/[C:14]/1=[N:22]\[C:23](=[O:35])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1[O:4][CH2:3][C:2]([OH:6])([CH3:5])[CH3:1])[CH2:10][CH2:11][CH3:12]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 684102-Methylpropane-1,2-diolHCID 178448621HCID 178448621、化合物

生成物 1

HCID 178448630HCID 178448630、化合物収率 35.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The product from Example 21A (91 mg, 1.01 mmol) in THF (2 mL) was treated with NaH (60%) (40.3 mg, 1.01 mmol) at room temperature for 20 minutes. To the above mixture was added the product from Example 20B (200 mg, 0.5 mmol) in THF (2 mL). After 4 hrs, the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate. 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 82.4 mg (35%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.04 (t, J=7.63 Hz, 3H) 1.38 (s, 6H) 1.48-1.55 (m, 2H) 1.89-1.97 (m, 2H) 4.03 (s, 2H) 4.54 (t, J=7.32 Hz, 2H) 4.62 (brs, 1H) 7.08 (d, J=8.85 Hz, 1H) 7.66 (d, J=4.58 Hz, 1H) 7.70 (dd, J=8.54, 2.14 Hz, 1H) 8.51 (d, J=5.19 Hz, 1H) 8.51 (s, 1H) 8.74 (s, 1H); MS (ESI+) m/z 468 (M+H)+.

後処理

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with ethyl acetate
  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-ad918ba7f76d400d8778e1426e903a75
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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