Hydrochloric Acid → HCID 117760214, compound

HRID 709748Notes

Reaction equation

HRID 709748 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH2:29][CH2:30][C:31]([O:33]C)=[O:32])[CH:26]=[CH:27][CH:28]=2)=[N:14][C:15]=1[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].[OH-].[Na+].Cl>CO>[CH3:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]1[N:14]=[C:13]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:26]=[CH:27][CH:28]=2)[CH:12]=[CH:11][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117759952HCID 117759952, compound

Product 1

HCID 117760214HCID 117760214, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)phenyl)propanoate (240 mg) in methanol (2.0 mL) was added 1N aqueous sodium hydroxide solution (1.0 mL), and the mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid (1.0 mL) was added to the reaction mixture, 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 (181 mg) as white crystals.

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-c140fe776f474e49b495f37178037a11
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…