Hydrochloric Acid → N-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)phenyl)-N-ethylglycine

HRID 709646Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 2-(ethyl(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)phenyl)amino)acetate (entire amount) in ethanol (3.0 mL) was added 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was stirred at 50° C. for 1 hr. 1N Hydrochloric acid was added, and the reaction 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 (90 mg) as pale-yellow crystals.

Workup

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

Sources & evidence

ORD record: ord-0f0ddb9884214a06a4260d8a6de5cf05
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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