Hydrochloric Acid → HCID 178477391, compound

Participants

Reaction Steps

To 15 ml. of dry acetonitrile were added 923 mg. (2 mmoles of 7-(α-aminophenylacetamido)-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and 1.62 grams (8 mmoles) of N,O-bis-trimethylsilylacetamide. Solution was complete within 5 minutes. To the mixture then were added 452 mg. (2.3 mmoles) of 2,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride. The temperature of the mixture rose about 4°and solution was complete within 5 minutes. After 20 minutes, a sample of the reaction mixture, analyzed by TLC, indicated that the reaction was complete. After two hours, the mixture (containing some solid) was slowly dropped into rapidly stirred ice water. A gummy solid deposited and was changed to particulate solid upon further stirring of the mixture. The suspension (pH 1.9) was adjusted to pH 1.7 by addition of concentrated hydrochloric acid. The mixture was filtered, and the solid was washed with dilute hydrochloric acid and air-dried to give 1.16 grams of the title compound as a buff-colored powder.

Provenance & Evidence