Potassium Carbonate → HCID 178490676, Verbindung

HRID 78539

Reaktionsgleichung

Reaktionsgleichung von HRID 78539
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O[CH2:33][C@@H:34]2[CH2:38][O:37][C:36](=[O:39])[NH:35]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[I-].C([N+](CC)(CC)CC)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:33][C@H:34]2[CH2:38][O:37][C:36](=[O:39])[NH:35]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 11032956(S)-(2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonateHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

Produkt 1

HCID 178490676HCID 178490676, VerbindungAusbeute 42,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6225Tetraethylammonium IodideKatalysatorHCID 67553Tetrabutylammonium IodideKatalysatorHCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of Example 244A (180 mg, 0.55 mmol), (S)-(2-oxo-oxazolidin-4-yl)methyl 4-methylbenzenesulfonate (180 mg, 0.67 mmol), potassium carbonate (153 mg, 1.1 mmol), tetrabutylammonium iodide (10 mg, 0.03 mmol), tetrabutylammonium hydrogen sulfate (10 mg, 0.03 mmol) and tetraethylammonium iodide (10 mg, 0.04 mmol) in toluene (35 mL) was refluxed for 14 h. The mixture was washed with water, brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography over silica gel (EtOAc as eluent) to afford 100 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (s, 9H), 3.92 (s, 3H), 4.11-4.26 (m, 2H), 4.30-4.41 (m, 2H), 4.57 (t, J=8.6 Hz, 1H), 6.33 (s, 1H), 6.62 (s, 1H), 6.93 (d, J=8.8 Hz, 1H), 7.35 (dd, J=9.0, 2.9 Hz, 1H), 7.79 (d, J=2.7 Hz, 1H). MS (DCI/NH3) m/z 424 (M+H)+.

Aufarbeitung

  1. washThe mixture was washed with water, brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography over silica gel (EtOAc as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-b5210208848d4ae0aced843378dcc55f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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