Hydroxylamine → HCID 54239818, compound

Participants

Reaction Steps

A solution of 2 g of distamycin A in 35 ml DMF was heated to 80° C. and treated with 0.46 ml of hydroxylamine 1M in DMF. After 30′ additional 1 equivalent of hydroxylamine 1M in DMF was added. The solution was evaporated to dryness and the crude residue was purified by flash chromatography (methylene chloride/methanol: 9/1) to give 1.50 g of 3-[1-methyl-4[1-methyl-4[1-methyl-4-formamidopyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidoxime which was dissolved in 50 ml of methanol and added of 10 ml of HCl 2N. The solution was stirred at room temperature for 2 days, the solvent evaporated in vacuo and the solid residue suspended in 200 ml of ethyl acetate, yielding, after filtration 1.4 g of the intermediate.

Provenance & Evidence