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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
ノート
印刷プレビュー

反応式

HRID 2191395 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-78b94bb0f076408e912981f3c94df44b
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329682B2

反応ノート

読み込み中…

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