O.Cl.C(OC([NH:10][C@@:11]1([C:35]([O:37]C(C)(C)C)=[O:36])[C@H:16]([CH2:17][S:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)[C@@H:15]([OH:27])[C@@H:14]2[C@H:12]1[C@H:13]2[C:28]([O:30]C(C)(C)C)=[O:29])=O)(C)(C)C.[OH-].[Na+]>O1CCOCC1>[NH2:10][C@@:11]1([C:35]([OH:37])=[O:36])[C@H:16]([CH2:17][S:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)[C@@H:15]([OH:27])[C@@H:14]2[C@H:12]1[C@H:13]2[C:28]([OH:30])=[O:29]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).
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