Hydroxylamine → HCID 54239818, compound

HRID 1018710Notes

Reaction equation

HRID 1018710 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18]3[CH:22]=[C:21]([C:23]([NH:25][CH2:26][CH2:27][C:28]([NH2:30])=[NH:29])=[O:24])[N:20]([CH3:31])[CH:19]=3)=[O:16])[N:12]([CH3:32])[CH:11]=2)=[O:8])=[CH:5][C:4]([NH:33][CH:34]=[O:35])=[CH:3]1.N[OH:37]>CN(C=O)C>[CH3:31][N:20]1[CH:19]=[C:18]([NH:17][C:15]([C:13]2[N:12]([CH3:32])[CH:11]=[C:10]([NH:9][C:7]([C:6]3[N:2]([CH3:1])[CH:3]=[C:4]([NH:33][CH:34]=[O:35])[CH:5]=3)=[O:8])[CH:14]=2)=[O:16])[CH:22]=[C:21]1[C:23]([NH:25][CH2:26][CH2:27][C:28](=[N:30][OH:37])[NH2:29])=[O:24]

Participants

4

Reactant 2

HCID 787Hydroxylamine2×HCID 3115Stallimycin

Product 1

HCID 54239818HCID 54239818, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe crude residue was purified by flash chromatography (methylene chloride/methanol: 9/1)

Sources & evidence

ORD record
ord-6130e5700b884cea889b9a64be593a56
Source dataset
uspto-grants-2002_11
Patent number
US06482920B1

Reaction notes

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