Trifluoroacetic acid → 2-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 1811188ノート

反応式

HRID 1811188 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:22])=[C:8](C(OC(C)(C)C)=O)[NH:9][C:10]=1[CH2:11][C:12]([OH:14])=[O:13])=[O:5])[CH3:2].FC(F)(F)C(O)=O.C(=O)=O.C(O)C.[OH-].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:22])=[CH:8][NH:9][C:10]=1[CH2:11][C:12]([OH:14])=[O:13])=[O:5])[CH3:2]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 19604758Methanedione--ethanol (1/1)HCID 498403275-carboxymethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

生成物 1

HCID 498403282-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester収率 85.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-30 °C

実験手順

A solution of 5-carboxymethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester (6.3 g, 20 mmol) in 600 ml of dichloromethane and trifluoroacetic acid (120 ml, 1.55 mol) was heated to reflux under a nitrogen atmosphere for 2.5 hours. The reaction mixture was stirred in the dry ice-ethanol bath and added with aqueous sodium hydroxide solution (1.55 mol sodium hydroxide in 100 ml of water) while maintaining the temperature at −30° C. Upon completion of the addition, the mixture was extracted with dichloromethane (100 ml×7). The combined organic extracts were washed with brine (100 ml), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-carboxymethyl-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (3.6 g, 85.7%) as a white solid.

後処理

  1. temperatureto reflux under a nitrogen atmosphere for 2.5 hours
  2. additionUpon completion of the addition
  3. extractionthe mixture was extracted with dichloromethane (100 ml×7)
  4. washThe combined organic extracts were washed with brine (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8cc79afed5e4490090664b5e6f5e2b5f
出典データセット
uspto-grants-2013_01
特許番号
US08362251B2

反応ノート

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