Acetone → HCID 87527374, compound

Participants

Reaction Conditions

Reaction Steps

Acetyl chloride (129.90 g, 1654.77 mmol) and pyridine (23.47 g, 296.67 mmol) were added to a solution of (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(amino)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicylo[4.2.0]oct-2-ene-2-carboxylate (100 g, 164.82 mmol) in dimethylacetamide (1300 ml) and the resulting mixture was stirred at 0-5° C. for 4 to 6 hours. The reaction mixture was then poured into excess acetone to form a slurry which was filtered and dried at room temperature overnight in vacuo to afford 97 g of crude (6R,7R)-7-[[(2Z)-2-(ethoxyimino)-2-[5-(acetamido)-1,2,4-thiadiazol-3-yl]acetyl]amino]-3-[[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl]-8-oxo-5-thia-1-azabicylo[4.2.0]oct-2-ene-2-carboxylate. 63% purity by HPLC area % assay (Luna 3 micron C18, 3.0 mm×50 mm; NH4OAc/CH3CN; 1.0 ml/min flow rate)

Provenance & Evidence