4-Des-dimethylaminotetracycline → HCID 71306420, compound

Participants

Reaction Steps

A solution was prepared by dissolving 20.0 g (50 mmoles) of 4-dedimethylaminotetracycline in 500 ml of a 15% aqueous ammonia solution. To the resulting solution 40 g of zinc dust was added and the mixture was vigorously stirred. After being stirred for twenty two (22) hours, the reaction mixture was filtered to remove excess zinc dust. The filtrate was neutralized with concentrated hydrochloric acid under ice-cooling. The precipitated solid was collected by filtration, washed with water, dried, and then purified and isolated by column chromatography, to provide 3.5 g of 4-dedimethylamino-12a-deoxytetracycline (yield: 18%) as a mixture of 2 isomers. The mixture was separated by HPLC to give isomer-A and isomer-B. Their properties are shown below.

Provenance & Evidence