Reaktion #546114

Reaktionsgleichung

Sodium methanethiolate

1,1-dioxo-3,3-dibutyl-4-oxo-5-(4-chlorophenyl)-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

→

title compound

Ausbeute 96.4%

1,1-Dioxo-3,3-dibutyl-4-oxo-5-(4-chlorophenyl)-7-methylthio-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine

Ausbeute 96.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated under reduced pressure
2. 2
   Extraktionthe residue was extracted with trichloromethane/water
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with brine
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   SonstigeThe crude product was purified by column chromatography

Vorschrift

Sodium methanethiolate (0.43 g, 6.08 mmol) was added to a solution of 1,1-dioxo-3,3-dibutyl-4-oxo-5-(4-chlorophenyl)-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 96; 0.66 g, 1.22 mmol) in anhydrous DMF (11 ml) under nitrogen. The reaction mixture was stirred at room temperature for 72 hours. The solvent was evaporated under reduced pressure and the residue was extracted with trichloromethane/water. The organic layer was separated, washed with brine, dried and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM as eluent to give the title compound 0.6 g (96%). NMR (500 MHz) 0.80–1.0 (m, 6H), 1.10–1.6 (m, 10H), 1.70–2.0 (m, 2H), 2.28 (s, 3H), 3.37–3.70 (m, 2H), 4.04 (s, 3H), 6.65 (s, 1H), 7.25–7.30 (m, 2H), 7.35–7.42 (m, 3H); m/z 510.4.

Quelle