Hydrochloric Acid → HCID 117760174, compound

HRID 1049537Notes

Reaction equation

HRID 1049537 reaction equation
C([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23]2[S:24][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[N:26][N:27]=2)[CH:9]=1)(=O)C(C)(C)C.[OH-].[Na+].O.Cl>CO.C1COCC1>[C:28]([C:25]1[S:24][C:23]([C:10]2[CH:9]=[C:8]([OH:7])[CH:13]=[CH:12][C:11]=2[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[N:27][N:26]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 117760193HCID 117760193, compound

Product 1

HCID 117760174HCID 117760174, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-(tert-butyl)-1,3,4-thiadiazol-2-yl)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-4-yl pivalate (191 mg) in methanol (2.0 mL) and THF (2.0 mL) was added 1N aqueous sodium hydroxide solution (1.3 mL), and the mixture was stirred at room temperature for 40 min. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (113 mg) as a white amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-290aefcb316a4220aac98fee233bb4b9
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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