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Methanol → 5-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

HRID 2191395
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HRID 2191395 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:25])=[C:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH:9][C:10]=1[CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[O:5])[CH3:2].CO.[OH-].[Li+]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:25])=[C:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH:9][C:10]=1[CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 498403922-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxopropyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate

생성물 1

HCID 592501015-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester수율 110.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-(2-Ethoxycarbonyl-ethyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1d (23.6 g, 66.8 mmol) was dissolved in 190 ml of tetrahydrofuran and 90 ml of methanol under stirring, and added with aqueous lithium hydroxide solution (80 ml, 10 mol/L, 0.8 mol) at room temperature. The color of the reaction solution gradually turned from light yellow to cyan, and stirred for another 1 hour. After thin lay chromatography showed the disappearance of starting materials, the resulting mixture was concentrated under reduced pressure to evaporate organic solvent. The residue was adjusted pH to 2 with hydrochloric acid solution (2 mol/L) in an ice-water bath under stirring. White precipitates were formed. The mixture was filtered, and the filter cake was dried to obtain the title compound 5-(2-carboxy-ethyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1e (24 g, yield 98%) as a white solid.

후처리

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. customto evaporate organic solvent
  3. customThe residue was adjusted pH to 2 with hydrochloric acid solution (2 mol/L) in an ice-water bath
  4. stirringunder stirring
  5. customWhite precipitates
  6. customwere formed
  7. filtrationThe mixture was filtered
  8. customthe filter cake was dried

출처 및 근거

ORD 기록
ord-78b94bb0f076408e912981f3c94df44b
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329682B2

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