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 1018713ノート

反応式

HRID 1018713 の反応式
[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]

参加物

5

反応物 3

HCID 3115Distamycin AHCID 7922Succinic anhydrideHCID 11430Potassium Carbonate

生成物 1

HCID 30543151H-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収率 77,749.898%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-59002045a7044448b34da85c498cc02f
出典データセット
uspto-grants-2002_11
特許番号
US06482920B1

反応ノート

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