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

HRID 2364979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2364979
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:24])=[C:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH:9][C:10]=1[CH2:11][C:12]([O:14]CC)=[O:13])=[O:5])[CH3:2].CO.[OH-].[Li+]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:24])=[C:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH:9][C:10]=1[CH2:11][C:12]([OH:14])=[O:13])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 498403265-ethoxycarbonylmethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

Produkt 1

HCID 498403275-carboxymethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl esterAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-ethoxycarbonylmethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester (30 g, 88.5 mmol) in tetrahydrofuran (268 ml), and methanol (134 ml) was added with aqueous lithium hydroxide solution (0.465 mol lithium hydroxide in 197 ml of water). Upon completion of the addition, the mixture was stirred for 1.5 hours at room temperature. The resulting mixture was concentrated under reduced pressure. The residue was added with water (200 ml) and extracted with ethyl ether. The water phase was adjusted to pH 1˜3 with 20% hydrochloric acid solution. The resulting solid was filtered, washed with ethyl ether, and dried in vacuo to give 5-carboxymethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester (20 g, 72.3%) as a yellow solid.

Aufarbeitung

  1. additionUpon completion of the addition
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was added with water (200 ml)
  4. extractionextracted with ethyl ether
  5. filtrationThe resulting solid was filtered
  6. washwashed with ethyl ether
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c059a8e7341442569c82ce833fe2e4c9
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697692B2

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