Ethyl bromopyruvate → diethyl 5-amino-1H-pyrrole-2,4-dicarboxylate

HRID 369864ノート

反応式

HRID 369864 の反応式
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6](=[NH:8])[NH2:7])[CH3:2].[CH2:10]([O:12][C:13](=[O:18])[C:14]([CH2:16]Br)=O)[CH3:11]>CN1C(=O)N(C)CCC1>[NH2:8][C:6]1[NH:7][C:14]([C:13]([O:12][CH2:10][CH3:11])=[O:18])=[CH:16][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:9]

参加物

4

反応物 2

HCID 66144Ethyl bromopyruvateHCID 4599837Carbamimidoyl-acetic acid ethyl ester

生成物 1

HCID 21262628diethyl 5-amino-1H-pyrrole-2,4-dicarboxylate

試薬・触媒・溶媒 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
60 °C

実験手順

At 0-5° C., 56.0 g (0.43 mol) of 2-amidino-acetic acid ethyl ester [for preparation see: Liebigs Ann. Chem., 1561 (1981)] are introduced into 172 ml of DMPU. 56.0 ml (0.45 mol) of bromopyruvic acid ethyl ester are added dropwise thereto within the course of 30 min and the reaction mixture is then heated at 60° C. for 3 hours. The dark-brown reaction solution is poured into 1 liter of ice-water and extracted with 1 liter of ethyl acetate and twice with a 0.5 liter of ethyl acetate each time. The organic phases are washed three times with a 0.5 liter of water and a 0.5 liter of brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2, hexane/ethyl acetate [1:1]) and crystallization from diethyl ether/hexane yield the title compound; m.p. 147-149° C.; MS: (M)+ =226.

後処理

  1. extractionextracted with 1 liter of ethyl acetate and twice with a 0.5 liter of ethyl acetate each time
  2. washThe organic phases are washed three times with a 0.5 liter of water
  3. dry with materiala 0.5 liter of brine, dried (Na2SO4)
  4. concentrationconcentrated by evaporation
  5. customColumn chromatography (SiO2, hexane/ethyl acetate [1:1]) and crystallization from diethyl ether/hexane

出典と根拠

ORDレコード
ord-2d7418f9d36e4742b1f9aafc72cf9455
出典データセット
uspto-grants-2000_10
特許番号
US06140332

反応ノート

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