Water → 4-(2-(11-Carboxyundecanoylamino)phenoxy)-butyric acid

HRID 1604408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604408
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][C:18]1[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:16])([O:3]C)=[O:2].O.[OH-].[Na+]>CO>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][C:18]1[CH:32]=[CH:31][CH:30]=[CH:29][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:16])([OH:3])=[O:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18796179Ethyl 4-(2-(11-carbomethoxyundecanoylamino)phenoxy)butyrate

Produkt 1

HCID 187958444-(2-(11-Carboxyundecanoylamino)phenoxy)-butyric acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of (8) (1.0 g, 2.22 mM) in methanol (100 mL) is added 1 mL of water followed by dropwise addition of 2.5 N sodium hydroxide solution (4.0 mL). The walls of the reaction flask are rinsed down with 10 mL of methanol and the mixture is stirred under a nitrogen atmosphere until TLC analysis shows no ester (mono- or di-) remaining. The methanol is removed in vacuo, the residue taken up in 100 mL of water, stirred for solution, filtered (20 mL water rinses), and the stirred filtrate acidified dropwise with 2 N hydrochloric acid. Filtration of the resultant precipitate followed by copious water washing and drying gave 0.87 g (96%) of (9) as a chalk-like white solid. The compound was one component by TLC (silica gel, the eluant was 10 mL of 2% methanol in methylene chloride containing 4 drops of glacial acetic acid). mp 128.5-130° C. uncorr.

Aufarbeitung

  1. washThe walls of the reaction flask are rinsed down with 10 mL of methanol
  2. customThe methanol is removed in vacuo
  3. stirringstirred for solution
  4. filtrationfiltered (20 mL water rinses)
  5. filtrationFiltration of the resultant precipitate
  6. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-73246bc00d9449079286cc6c64e95949
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994362

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