Diisopropyl Ether → HCID 21426455, compound

Participants

Reaction Conditions

Reaction Steps

The sodium salt 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 (12 g.) is dissolved in water (22 cc.). Potassium thiocyanate (29 g.), sodium bicarbonate (2.45 g.) and 1-tert-butyl-5-thioxo-1,2,3,4-tetrazoline (4.6 g.) are added to this solution and the mixture is heated to 60° C. for 6 hours. After cooling, the reaction mixture is diluted with water (150 cc.) and washed with ethyl acetate (200 cc.) after having been acidified to pH 5.5 by adding 4 N hydrochloric acid. The mixture is then acidified to pH 1.5 by adding 4 N hydrochloric acid in the presence of ethyl acetate (350 cc.). After decanting the organic phase, the aqueous phase is extracted twice with ethyl acetate (a total of 150 cc.). The organic extracts are combined, washed twice with water (a total of 300 cc.), dried over sodium sulphate, treated with decolourising charcoal, filtered and then concentrated to dryness under reduced pressure (20 mm Hg). The residue obtained is dissolved in tetrahydrofuran (60 cc.) and this solution is then poured into isopropyl ether (600 cc.). A product precipitates, which is isolated by filtration and dried under reduced pressure (0.1 mm Hg) to give 2-carboxy-8-oxo-7-[(1,3-dithiol-2-on-4-yl)-acetamido]-3-[(1-tert-butyl-1,2,3,4-tetrazol-5-yl)-thiomethyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene (4.5 g.).

Provenance & Evidence