Sodium hydride → HCID 178448630, Verbindung

HRID 340649

Reaktionsgleichung

Reaktionsgleichung von HRID 340649
[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]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 684102-Methylpropane-1,2-diolHCID 178448621HCID 178448621, Verbindung

Produkt 1

HCID 178448630HCID 178448630, VerbindungAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ad918ba7f76d400d8778e1426e903a75
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895592B2

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