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 418097Notes

Reaction equation

HRID 418097 reaction equation
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]

Participants

6

Reactant 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

Product 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 AcidYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

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.

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

Sources & evidence

ORD record
ord-0222d241064b4bcb860aee1a60dcbeea
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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