Hydrochloric Acid → (1S,2R,3S,4S,5R,6R)-2-Amino-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid hydrochloride

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Reaction Conditions

Reaction Steps

A mixture of water (430 mL) and 37% HCl in water (299.9 mL, 3.65 mol) is added to a suspension of di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (215 g, 365.3 mmol) in 1,4-dioxane (73.1 mL). The resulting slurry is stirred at 100° C. for 4.5 hours, cooled to 25° C. and concentrated in vacuo to provide a white solid. Triturate sequentially with methyl tert-butyl ether (2 L) and hexanes (2 L) and then filter to collect the solids. Dry under vacuum for 16 hours. The solid is washed again with methyl tert-butyl ether (2×1 L) and hexane (1 L), then dried under vacuum at 50° C. overnight to yield the title compound as a white solid (140.4 g, 93% yield). MS (m/z): 376/378 (M+1).

Provenance & Evidence