1,1,3,3-Tetramethylguanidine → HCID 178483393, compound

Participants

Reaction Steps

To a stirred suspension of 122 mg of (E)-(6R,7R)-3-[3-[(3-amino-propyl)-dimethyl-ammonio]-propenyl-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid chloride monohydrochloride in 2 ml of dimethylsulfoxide was added 60 mg of 1H-1,2,4-triazole-1-carboximidamide monohydrochloride followed by 0.05 ml of tetramethylguanidine. The mixture was stirred for 2 h at 20° and then subjected to chromatographic purification on MCI gel CHP20P using a gradient of 0-30% aqueous acetonitrile for elution. The product-containing fractions were concentrated in vacuo and freeze-dried, and the remaining amorphous material was triturated with 10 ml of a 0.4 N solution of hydrochloric acid in diethyl ether. The white solid was isolated by filtration, washed with 20 ml of diethyl ether and dried to give 48 mg of (E)-(6R,7R)-3-[3-[(3-guanidino-propyl)-dimethyl-ammonio]-propenyl]-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid chloride monohydrochloride as a white solid.

Provenance & Evidence