Stallimycin → 1H-Pyrrole-2-carboxamide, N-(5-(((2-cyanoethyl)amino)carbonyl)-1-methyl-1H-pyrrol-3-yl)-4-(((4-(formylamino)-1-methyl-1H-pyrrol-2-yl)carbonyl)amino)-1-methyl-, hydrate

HRID 1018713Notes

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](N)=[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.C1(=O)OC(=O)CC1.C([O-])([O-])=O.[K+].[K+]>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:29])=[O:24]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1 g of distamycin A in 20 ml DMF were added 550 mg of succinic anhydride and 950 mg of K2CO3. The solution was heated at 60° C. for 3 hours then evaporated to dryness and the crude residue was purified by flash chromatography (methylene chloride/methanol: 9/1) to give 750 g of 3-[1-methyl-4[1-methyl-4[1-methyl-4-formamidopyrrole-2-carboxamido]pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionitrile which was dissolved in 20 ml of methanol and added of 5 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 20 ml of ethyl acetate, yielding, after filtration 560 mg of the intermediate.

Workup

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

Sources & evidence

ORD record: ord-59002045a7044448b34da85c498cc02f
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482920B1

Reaction notes

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