Sodium Azide → HCID 21426466, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (0.871 g.) is added to a solution of 3-acetoxymethyl-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (3 g.) in water (60 cc.) and sodium bicarbonate (0.588 g.), and the mixture is heated to 50° C. for 16 hours. It is allowed to cool and sodium bicarbonate (0.4 g.) is added. The mixture is extracted twice with ethyl acetate (40 cc.). The aqueous phase is treated with decolourising charcoal and brought to pH 2 by adding 6 N hydrochloric acid. A product precipitates, and is extracted with ethyl acetate (240 cc.). The organic extracts are dried over sodium sulphate and then concentrated to dryness under reduced pressure (20 mm.Hg). A residue (1.9 g.) is obtained, which is recrystallised from acetonitrile (18 cc.) to give 3-azidomethyl-2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (1.29 g.), m.p. 160° C., after a further recrystallisation from acetonitrile.

Provenance & Evidence