Acetic Acid → HCID 11645253, compound

Participants

Reaction Conditions

Reaction Steps

A 5 mL microwave tube was charged with 4 mL AcOH, 1-1 (0.50 g, 2 mmol), and hydrazine monohydrate (0.2 mL, 3.93 mmol). The tube was sealed and heated in a Personal Chemistry microwave apparatus for 15 min at 175° C. LC/MS analysis indicated two new products with the same molecular weight. The reaction was diluted with EtOAc and neutralized with 200 mL saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. The remaining oil was absorbed onto silica gel and the diastereomers were separated on an Isco automated system affixed with a Biotage Flash 25(M) cartridge eluting at 20 mL/min with 15% EtOAc in hexane over 1 h. The diastereomer with the higher inhibitory activity (the cis) eluted second.

Provenance & Evidence