Hydrochloric Acid → HCID 67119157, compound

HRID 2076616Notes

Reaction equation

HRID 2076616 reaction equation
[OH-].[Na+].CO.[OH:5][C:6]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[C:15]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][C:34]([CH2:37][C:38]([O:40]C)=[O:39])=[C:33]([CH3:42])[CH:32]=3)=[CH:27][CH:26]=2)[C:7]=1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl>O1CCCC1>[C:11]([O:10][C:8]([C:7]1[C:6]([OH:5])=[C:18]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:16][C:15]=1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][C:38]([OH:40])=[O:39])=[C:33]([CH3:42])[CH:32]=2)=[CH:27][CH:26]=1)=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 67119154HCID 67119154, compound

Product 1

HCID 67119157HCID 67119157, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1N aqueous sodium hydroxide solution (3.0 ml, 3.0 mmol) and methanol (0.5 ml) were added to a solution of tert-butyl 2-hydroxy-6-[({4′-[(methoxycarbonyl)methyl]-3′-methyl-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (667 mg, 1.26 mmol) obtained in Example (17-3) in tetrahydrofuran (8.5 ml), and the mixture was stirred at room temperature for 6 hours. After the reaction mixture was poured into 0.5N 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 residue obtained by removing the solvent under reduced pressure was crystallized from a mixture solvent of ethanol-ethyl acetate to give the title compound as a colorless powder (552 mg, yield: 84%).

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 residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas crystallized from a mixture solvent of ethanol-ethyl acetate

Sources & evidence

ORD record
ord-46ca073d359943e9b5c7a1a0edc5c7a8
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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