Hydrochloric Acid → HCID 11555148, compound

HRID 2076591Notes

Reaction equation

HRID 2076591 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[C:13]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38]C)=[O:37])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl>O1CCCC1>[C:9]([O:8][C:6]([C:5]1[C:4]([OH:3])=[C:16]([C:17]([F:18])([F:19])[F:20])[CH:15]=[CH:14][C:13]=1[CH2:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]([OH:38])=[O:37])=[CH:31][CH:30]=2)=[CH:27][CH:28]=1)=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67119193HCID 67119193, compound

Product 1

HCID 11555148HCID 11555148, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3N aqueous sodium hydroxide solution (0.33 ml, 0.33 mmol) was added to a solution of tert-butyl 2-hydroxy-6-[({4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (467 mg, 0.90 mmol) obtained in Example (6-9) in tetrahydrofuran (8 ml), and the mixture was stirred at room temperature for 10 hours. After the reaction mixture was poured into 1N hydrochloric acid and the mixture was extracted with ethyl acetate (three times), the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solid obtained by removing the solvent under reduced pressure was reprecipitated using n-hexane-ethyl acetate to give the title compound as a white powder (372 mg, yield: 82%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (three times)
  2. washthe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe solid obtained
  5. customby removing the solvent under reduced pressure
  6. customwas reprecipitated

Sources & evidence

ORD record
ord-5a7d364018bf4f6fa5a86168b9bb93ae
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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