Hydrochloric Acid → 4-(2-(2-Carboxy-ethyl)-3-{6-[3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-5-methanesulfonyl-phenoxy]-hexyl}-phenoxy)-butyric Acid

HRID 418097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418097
C([O:3][C:4](=[O:50])[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]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24]([C:32]3[CH:42]=[CH:41][C:35]4[O:36][C:37]([F:40])([F:39])[O:38][C:34]=4[CH:33]=3)[CH:23]=2)[C:10]=1[CH2:43][CH2:44][C:45]([O:47]CC)=[O:46])C.[OH-].[Na+].Cl>C(O)C.O>[C:45]([CH2:44][CH2:43][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH3:31])(=[O:29])=[O:30])[CH:25]=[C:24]([C:32]3[CH:42]=[CH:41][C:35]4[O:36][C:37]([F:40])([F:39])[O:38][C:34]=4[CH:33]=3)[CH:23]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:50])=[O:3])([OH:47])=[O:46]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 578630564-[3-{6-[3-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-5-methanesulfonyl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl Ester

Produkt 1

HCID 442191604-(2-(2-Carboxy-ethyl)-3-{6-[3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-5-methanesulfonyl-phenoxy]-hexyl}-phenoxy)-butyric AcidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 4-[3-{6-[3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-5-methanesulfonyl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.0 g) in ethanol (8 mL) was added a solution of NaOH (556 mg) in water (4 mL) and the resulting mixture was stirred at room temperature for 3 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 and concentrated under reduced pressure to give an oil which was crystallized from ethyl acetate/hexanes mixture to yield the title compound (0.8 g, 87% yield). HRMS calcd for C33H36O10F2S [M+Na]+ 685.1889, observed 685.1892.

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. customto give an oil which
  7. customwas crystallized from ethyl acetate/hexanes mixture

Quellen und Nachweise

ORD-Eintrag
ord-0222d241064b4bcb860aee1a60dcbeea
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093253B2

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