Water → t-butyl 4-(methylsulfonyl)-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

HRID 516235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516235
[O:1]1[C:22]2[C:5](=[CH:6][C:7]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9][C:8]=3[CH:21]=2)[NH:4][CH2:3][CH2:2]1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(C(C)C)CC)(C)C.O>ClCCl>[CH3:23][S:24]([N:4]1[C:5]2=[CH:6][C:7]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][CH2:9][C:8]=3[CH:21]=[C:22]2[O:1][CH2:2][CH2:3]1)(=[O:26])=[O:25]

Komponenten

6

Edukt 4

HCID 962WaterHCID 31297Methanesulfonyl chloride2×HCID 81531Diisopropylethylamine2×HCID 66982245t-butyl 3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

Produkt 1

HCID 58494859t-butyl 4-(methylsulfonyl)-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 130 mg of t-butyl 3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate in 4 ml of dichloromethane were added 0.036 ml of methanesulfonyl chloride and 0.089 ml of diisopropylethylamine under ice-cooling, followed by stirring at room temperature for 16 hours. To the reaction mixture were added 0.036 ml of methanesulfonyl chloride and 0.089 ml of diisopropylethylamine, followed by stirring at room temperature for additional 9 hours. To the reaction mixture was added water, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 152 mg of t-butyl 4-(methylsulfonyl)-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate as a colorless solid.

Aufarbeitung

  1. temperaturecooling
  2. stirringby stirring at room temperature for additional 9 hours
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-09bb9ae1013544099b21292ea7120df0
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108977B2

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