Phenylacetyl chloride → HCID 12895273, compound

Participants

Reaction Steps

To a suspension of p-nitrobenzyl 7-(2-carboxybenzamido)-3-methyl-3-cephem-4-carboxylate (462 mg., 1 mmol.) in tetrahydrofuran at 0° C. is added triethylamine (0.14 ml., 1 mmol.). After 15 minutes, ethyl chloroformate (0.1 ml., 2 mmol.) is added, and then after 0.5 hour at 0° C., anhydrous hydrazine (0.03 ml., 1 mmol.) is added to the reaction mixture. After 15 minutes, the mixture is filtered, and the filtrate is evaporated to dryness in vacuo. The residue is taken up in acetone (15 ml.) and tetrahydrofuran (15 ml.), and phenylacetyl chloride (0.13 ml., 1 mmol.) is added. After refluxing for 30 min., the mixture is cooled and evaporated in vacuo to dryness. The product is taken up in chloroform (50 ml.) and washed successively with 1N HCl (30 ml.), 10% sodium bicarbonate (40 ml.), and brine (40 ml.), dried over MgSO4, and evaporated in vacuo to dryness. The colorless product is slurried with ethyl acetate (12 ml.). Filtration gives p-nitrobenzyl 7-phenylacetamido-3-methyl-3-cephem-4-carboxylate. Recrystallization from ethyl acetate gives an analytical sample: m.p. 227°-230°.

Provenance & Evidence