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

HRID 1811188

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: -30 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-8cc79afed5e4490090664b5e6f5e2b5f
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08362251B2

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