Réaction #50866

Équation de réaction

ammonia

Triethyl amine

diacid

5-(3-((7-CHLOROQUINOLIN-2-YL-METHYL)OXY)PHENYL)-4,6-DITHIANONANEDIOIC ACID

2-chloro-1-methylpyridinium iodide

→

title compound

8-CARBAMYL-5-(3-(7-CHLOROQUINOLIN-2-YLMETHOXY)PHENYL)-4,6-DITHIAOCTANOIC ACID

Solvants

Water

CH2Cl2 CH3CN

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture stirred for another hour at 10° C
2. 2
   ExtractionExtraction with CH2Cl2 (2×) and EtOAc (2×) and flash chromatography of the residue on silica with acetone: CH2Cl2 :AcOH 40:60:1 and 50:50:1

Mode opératoire

The diacid (Example 3) (3.954 g, 8.04 mmoles) was dissolved in 250 mL CH2Cl2 :CH3CN 4:1. Triethyl amine (2.5 mL, 2.2 equiv.) was added followed, at 0° C., by 2-chloro-1-methylpyridinium iodide (2.257 g, 1.1 equiv.). After stirring 1 hour at 0° C., ammonia was added and the mixture stirred for another hour at 10° C. Water was then added and the aqueous layer acidified to pH 5. Extraction with CH2Cl2 (2×) and EtOAc (2×) and flash chromatography of the residue on silica with acetone: CH2Cl2 :AcOH 40:60:1 and 50:50:1 afforded the title compound.

Source