Triethylamine → HCID 86741964, compound

Participants

Reaction Conditions

Reaction Steps

In 50 ml of DMF were dissolved 1.67 g of methyl (±)cis-3-azido-4-oxo-2-azetidinecarboxylate (29) and 1.86 g of p-toluenesulfonic acid monohydrate and, 400 mg of 10% Pd-C was added to the solution followed by hydrogenation at ambient temperature under atmospheric pressure of hydrogen. The catalyst was filtered off and the solvent was removed by distillation under reduced pressure to obtain a viscous oil. The oil was dissolved in 80 ml of methylene chloride. The solution was cooled to -10° C. and, 2.89 ml of triethylamine and 0.736 ml of acetyl chdloride were added to the solution in sequence. The mixture was stirred at the same temperature for 1 hour and 20 minutes. The reaction mixture was concentrated under reduced pressure and the residue was subjected to column chromatography using 100 g of silica gel. By eluting with ethyl acetate-methanol (10:1), 683 mg of methyl (±)cis-3-acetylamino-4-oxo-2-azetidinecarboxylate (31) was obtained as a white solid.

Provenance & Evidence