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

HRID 369864노트

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HRID 369864 반응식
[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]

참가 물질

4

반응물 2

HCID 66144Ethyl bromopyruvateHCID 4599837Carbamimidoyl-acetic acid ethyl ester

생성물 1

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

시약·촉매·용매 1

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

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2d7418f9d36e4742b1f9aafc72cf9455
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140332

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