Hydrochloric Acid → HCID 131710692, compound

Participants

Reaction Steps

The hydrochloride of 3-acetoxymethyl-7β-aminoceph-2-em-4α-carboxylic acid (1.5 g., 0.05 m.mol) was heated in refluxing dry chloroform (20 ml) containing hexamethyldisilazane (3.2 ml. 0.015 mol) for 1 hr. The excess silylating reagent and solvent were removed under high vacuum. The resulting gum was redissolved in dry ethyl acetate (20 ml) and 2,6-dichlorobenzoyl chloride (1.0 g 0.45 mmol) added. the reaction was carried out for 1 hr. at reflux. Treatment of the organic phase with dilute hydrochloric acid, water, drying and evaporation gave a gum. Addition of a solution of 10% sodium 2-ethylhexanoate in ethyl acetate precipitated a sodium salt, νmax (Nujol) 3300 (NH), 1760 (β-lactam), 1720 (acetate), 1660 (amide) and 1605 cm-1 (--CO2Na), RF (system 3) 0.53 (with an impurity, RF 0.19). These properties are consistent with the structure of the compound named in the title.

Provenance & Evidence