Ethyl Acetate → HCID 59287096, Verbindung

HRID 2045712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045712
C([O-])([O-])=O.[Cs+].[Cs+].[Br:7][C:8]1[C:9](=[O:20])[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[CH:12]=2.BrC1C=CC(S(O[C@@H:32]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]2)(=O)=O)=CC=1.CCOC(C)=O>CN1C(=O)CCC1.O>[Br:7][C:8]1[C:9]([O:20][C@H:32]2[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:34]([C:44]([O:46][CH3:47])=[O:45])[CH2:33]2)=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[CH:12]=2

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 59287022HCID 59287022, Verbindung

Produkt 1

HCID 59287096HCID 59287096, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Cs2CO3 (2.11 g, 6.46 mmol) was added to a solution of 3-bromo-7-methoxyquinolin-2(1H)-one (1.31 g, 5.17 mmol) and 1-text-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (2.0 g, 4.31 mmol) in NMP (21.5 mL), and the reaction mixture was stirred for 40 h at 40° C. An additional portion of 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (1.0 g, 2.16 mmol) was added, and the reaction mixture was stirred at 40° C. for 16 h. The reaction mixture was cooled and poured onto a mixture of EtOAc and water, and the layers were separated. The organic layer was washed with water twice, NaHCO3 twice and brine, dried over Mg2SO4, filtered and concentrated. The product was used with no further purification. LRMS (M+H-Boc)+=381.2.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 40° C. for 16 h
  2. temperatureThe reaction mixture was cooled
  3. customthe layers were separated
  4. washThe organic layer was washed with water twice
  5. dry with materialNaHCO3 twice and brine, dried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was used with no further purification

Quellen und Nachweise

ORD-Eintrag
ord-3a1ea12aedf74109bc27aa6c6b901734
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591878B2

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