Azidamfenicol

UsesAzidamfenicol is a semi-synthetic chloramphenicol in which the nitro moiety is replaced with a methylsulphone and the dichloroacetamide is replaced with azidoacetamide, first synthesised at Bayer in 1959. Azidamfenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Azidamfenicol acts by binding to the 23S sub-unit of the 50S ribosome, inhibiting protein synthesis. Azidamfenicol has received little research attention with only a few literature citations.

Preparation21.2 g of D-(-)-threo-1-p-nitrophenyl-2-aminopropane-1,3-diol was mixed with 10 g of azide acetonitrile (BP 68℃/25 mm) in a mixture of 125 ml methanol and 125 ml water, and stirred for several days at 30-40℃. The mixture was filtered off from a small amount of insoluble alkali, and the solvent was distilled under vacuum. The residue was treated with a small amount of hydrochloric acid until it reached Congo red, and extracted with ethyl acetate. azidamfenicol was given by solvent evaporation and recrystallization at MP 107℃.