Pyridine → HCID 70604455, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-triphenylmethylamino-2,2-dimethyl-3-carbamylpenam (11.01 g., 0.024 mole), dry pyridine (4.9 g., 0.062 mole) and dry chloroform (250 ml.) is stirred for five minutes and the resulting solution cooled to 0° C. in a wet ice/acetone bath. Phosgene (8.8 ml. of 3.41 molar solution in chloroform) is added by means of a syringe. The reaction mixture is stirred at 5° C. for ten minutes after which the cooling bath is removed and the reaction mixture allowed to warm to room temperature. It is stirred for 30 minutes and then washed successively with water (300 ml.), 1N hydrochloric acid (300 ml.), and water (300 ml.). The chloroform solution is dried (MgSO4), treated with activated charcoal, and filtered through diatomaceous earth. The filtrate is concentrated to reduced pressure and the residue taken up in methylene chloride (450 ml.). The methylene chloride solution is washed successively with 1N hydrochloric acid (150 ml.) and water (300 ml.) and then dried using anhydrous sodium sulfate. The dried solution is then filtered and concentrated under reduced pressure to give the product as a golden foam (7.1 g., 67.3%).

Provenance & Evidence