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

HRID 417044Notes

Reaction equation

HRID 417044 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]3[CH:38]=[CH:37][C:31]4[O:32][C:33]([F:36])([F:35])[O:34][C:30]=4[CH:29]=3)[CH:25]=[C:24]([C:39](=[O:41])[CH3:40])[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>[C:39]([C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([C:28]2[CH:38]=[CH:37][C:31]3[O:32][C:33]([F:35])([F:36])[O:34][C:30]=3[CH:29]=2)[CH:25]=1)[O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:11]1[C:10]([CH2:42][CH2:43][C:44]([OH:46])=[O:45])=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:49])=[O:3])(=[O:41])[CH3:40]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594967934-[3-{6-[3-Acetyl-5-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-phenoxy]hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 469291674-[3-{6-[3-Acetyl-5-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric acidYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4-[3-{6-[3-acetyl-5-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (300 mg) in ethanol (5 mL) was added a solution of NaOH (176 mg) in water (2 mL) 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 137 mg of the title compound (50% yield). HRMS calcd for C34H36O9F2 [M+Na]+ 649.2219, observed 649.2222.

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-e04398da1c6b4543a745eb71038fa31f
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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