Isobutyl carbamate → HCID 21877961, Verbindung

HRID 896136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896136
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=2[F:15])[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:21](=[O:28])([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])N>C1COCC1.O>[S:1]1[CH2:2][CH:3]=[C:4]([C:7]2[C:8]([F:15])=[CH:9][C:10]([NH:14][C:21](=[O:28])[O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:11][C:12]=2[F:13])[CH2:5][CH2:6]1

Komponenten

5

Edukt 3

HCID 10973Isobutyl carbamateHCID 516892Sodium BicarbonateHCID 21876582HCID 21876582, Verbindung

Produkt 1

HCID 21877961HCID 21877961, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirred, biphasic mixture of 4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorobenzenamine (Step 4, 3.90 g, 17.2 mmol) in THF/water (2:1, 103 mL) is added sodium bicarbonate (2.88 g, 34.3 mmol) followed by isobutyl carbamate (2.45 mL, 18.9 mmol) dropwise. The reaction mixture is stirred at ambient temperature for 7 h and is then concentrated under reduced pressure, diluted with EtOAc (100 mL) and H2O (50 mL), and the layers are separated. The organic phase is washed with H2O (25 mL) and saline (25 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by chromatography on a Biotage Flash 40M 90 g silica gel cartridge, eluting with 5-10% EtOAc/Hexanes, affords the title compound, mp 136-137° C.; MS (ESI−) for C16H19F2NO2S m/z 326 (M−H)−.

Aufarbeitung

  1. concentrationis then concentrated under reduced pressure
  2. additiondiluted with EtOAc (100 mL) and H2O (50 mL)
  3. customthe layers are separated
  4. washThe organic phase is washed with H2O (25 mL) and saline (25 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by chromatography on a Biotage Flash 40M 90 g silica gel cartridge
  8. washeluting with 5-10% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-797685828ced4951912726513a597587
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919329B2

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