1,2-Dichloroethane → HCID 89455885, compound

Participants

Reaction Steps

A mixture of 2-((4-(N-(tert-butoxycarbonyl)methylsulfonamido)benzyl)-(methyl)amino)acetic acid (0.398 g, 1.069 mmol), (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.345 g, 0.822 mmol), EDC (0.473 g, 2.466 mmol), and DMAP (0.151 g, 1.233 mmol) in DCM was stirred at RT for 30 minutes. CH3CN (10 ml) and DMF (5 ml) were added to dissolve insoluble residue, and the mixture was stirred at RT for 2 days. The mixture was diluted with DCM and washed twice with HCl 1N and with NaHCO3. The organic layer was dried over Na2SO4, and the solvent was removed. The crude was purified by filtration on SCX cartridge (DCM/MeOH 1/1; MeOH/conc.aq.NH4OH 90/10). The basic fraction was portioned between EtOAc and water, and the organic phase was washed with brine and dried over Na2SO4. The solvent was removed, and the crude (S)-4-(2-(2-((4-(N-(tert-butoxycarbonyl)-methylsulfonamido)benzyl)(methyl)amino)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide was obtained as a colorless amorphous solid (0.250 g, 0.323 mmol, 39.3% yield, MS/ESI+ 774.5 [MH]+) and used in the next step without any further purification.

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