1,2-Dichloroethane → HCID 86679587, compound

Participants

Reaction Steps

3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (5 g, 11.90 mmol), (R)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (4.73 g, 17.85 mmol), DMAP (1.599 g, 13.09 mmol), and EDC (4.56 g, 23.80 mmol) were dissolved in DMF (5 ml). The reaction was stirred at RT for 2 hours to achieve completion. The reaction mixture was diluted with water, and the precipitate was filtered, washed with water, dissolved in DCM and extracted with HCl 1N, Na2CO3 sat. sol. and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum. The crude product was crystallized in EtOH to give 4-((S)-2-((R)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (3.2 g, 4.79 mmol, 40.3% yield).

Provenance & Evidence