Acetyl chloride → 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

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Reaction Steps

Acetyl chloride (334.31 μL, 368.75 mg, 4.70 mmol) in dichloromethane (5 mL) is added to a stirring, cooled solution of di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.30 g, 3.91 mmol) and triethylamine (709.32 μL, 514.97 mg, 5.09 mmol) in dichloromethane (19.57 mL) at 0° C. then stirred. After 90 minutes, dilute with water and extract with dichloromethane (3×25 mL). The combined organic extracts are dried over magnesium sulfate, filtered, and concentrated under reduced pressure giving the title compound (2.40 g, 3.81 mmol, 97%): MS (m/z): 653 (M+1).

Provenance & Evidence