1,2-Dichloroethane → HCID 86679551, compound

Participants

Reaction Steps

4-(2-(N-(5-((carboxymethylthio)carbonyl)-2-methoxyphenyl)-methylsulfonamido)-ethyl)morpholin-4-ium 2,2,2-trifluoroacetate (0.194 g, 0.355 mmol) was suspended in dry DCM (3.5 ml), and (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.115 g, 0.273 mmol), EDC (0.157 g, 0.819 mmol), and DMAP (0.0667 g, 0.546 mmol) were sequentially added with stirring at RT under nitrogen. The resulting yellow solution was stirred at the same temperature for 24 hours. The mixture was diluted with DCM and washed twice with 1N HCl and then with brine. The organic phase was dried over Na2SO4, and the solvent was removed under vacuum. The crude was purified by flash chromatography on silica gel column (DCM:MeOH=96:4) followed by preparative HPLC under neutral conditions. The fraction obtained after solvent evaporation was dissolved in Et2O and HCl in Et2O was added; the resulting suspension was stirred at RT for few minutes. The volatiles were removed, and the residue was dried affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)benzoylthio)acetoxy)-ethyl)pyridine 1-oxide hydrochloride (0.103 g, 0.118 mmol, 43.3% yield, LC-MS purity (BPI): 99.7%, MS/ESI+ 834.34 [MH]+, [αD]=−54.00, c=0.5, MeOH).

Provenance & Evidence