Reaktion #1109904

Reaktionsgleichung

sodium hydride

tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

methyl 6-chloropicolinate

sodium iodide

→

title compound

Ausbeute 37.7%

tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-{[6-(methoxycarbonyl)pyridin-2-yl]oxy}-1,4-oxazepane-4-carboxylate

Ausbeute 37.7%

Lösungsmittel

DMF

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUnder ice-cooling
2. 2
   workup.STIRRINGthe mixture was stirred at the same temperature for 1 hr
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe extract was washed with brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

Under ice-cooling, sodium hydride (60% in oil, 53 mg) was added to a solution of tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate (400 mg) in DMF (5 mL). After stirring at room temperature for 20 min, methyl 6-chloropicolinate (280 mg) and sodium iodide (330 mg) were added, and the mixture was stirred at the same temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (207 mg).

Quelle