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

HRID 417049Notes

Reaction equation

HRID 417049 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-674b5e7dcbb34449a19b6eb9be18df62
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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