Hydrochloric Acid → 4-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid

HRID 417049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417049
C([O:3][C:4](=[O:49])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[CH:25]=[C:24]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[CH:23]=2)[C:10]=1[CH2:42][CH2:43][C:44]([O:46]CC)=[O:45])C.[OH-].[Na+].Cl>C(O)C.O>[O:37]1[C:36]2[CH:40]=[CH:41][C:33]([C:24]3[CH:23]=[C:22]([CH:27]=[C:26]([C:28](=[O:32])[CH:29]([CH3:30])[CH3:31])[CH:25]=3)[O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:11]3[C:10]([CH2:42][CH2:43][C:44]([OH:46])=[O:45])=[C:9]([CH:14]=[CH:13][CH:12]=3)[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:49])=[O:3])=[CH:34][C:35]=2[O:39][CH2:38]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594968284-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Produkt 1

HCID 469291684-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acidAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-[3-[6-(3-benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (191 mg) in ethanol (2 mL) was added 10 M NaOH (566 μL) and the resulting mixture was stirred at room temperature for 5 h. Then the reaction mixture was diluted with water, acidified with 3 N HCl and extracted into ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified on a reverse-phase HPLC to yield 50 mg of the title compound (29% yield). HRMS calcd for C36H42O9 [M+Na]+ 641.2721, observed 641.2720.

Aufarbeitung

  1. extractionextracted into ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified on a reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-674b5e7dcbb34449a19b6eb9be18df62
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088936B2

Notizen zur Reaktion

Wird geladen…