Acetic Acid → (1S,2R,3R,4S,5R,6S)-4-(Acetylamino)-2-amino-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-(acetylamino)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.40 g, 3.81 mmol) is added to acetic acid (7.99 g, 7.62 mL, 133.05 mmol,) and water (3.81 mL, 3.81 g, 211.60 mmol) and heated in a microwave to 140° C. After 15 minutes, cool to room temperature, dilute with water and filter to collect the solids. Sequentially wash the solids with water (2×50 mL) and diethyl ether (2×50 mL), and then dry in a vacuum oven giving the title compound (1.23 g, 2.95 mmol, 77%): MS (m/z): 417/419 (M+1).

Provenance & Evidence