Distamycin A → 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 1018713Notizen

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-59002045a7044448b34da85c498cc02f
Quelldatensatz: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06482920B1

Notizen zur Reaktion

Wird geladen…