Hydrochloric Acid → LY-3020371

Participants

Reaction Conditions

Reaction Steps

Water (1.10 L) and 12.18M hydrogen chloride in water (789.88 mL, 9.62 mol) is added to a solution of di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-{[(3,4-difluorophenyl)sulfanyl]methyl}-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (550.00 g, 962.07 mmol) in 1,4-dioxane (192.41 mL). The resulting slurry is stirred at 100° C. After 12 hours, the reaction is then cooled to 25° C., stirred for 12 hours, and then basified with NaOH (50% wt/wt) to pH=2.65. The resulting mixture is stirred at 10° C. for 30 minutes whereupon the precipitate is collected by filtration, washed with water (1 L) and methyl tert-butyl ether (1 L), and dried for 2 hours at 25° C., and then at 60° C. in a oven until constant weight to yield the title compound (300 g, 87% yield). MS (m/z): 360 (M+1).

Provenance & Evidence