Hydrochloric Acid → HCID 117759778, compound

HRID 1049548Notes

Reaction equation

HRID 1049548 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([C:30]4[CH:35]=[C:34]([O:36][CH:37]5[CH2:42][CH2:41][CH2:40][CH2:39][O:38]5)[CH:33]=[CH:32][C:31]=4[F:43])=[C:23]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([C:30]4[CH:35]=[C:34]([O:36][CH:37]5[CH2:42][CH2:41][CH2:40][CH2:39][O:38]5)[CH:33]=[CH:32][C:31]=4[F:43])=[C:23]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117759745HCID 117759745, compound

Product 1

HCID 117759778HCID 117759778, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-cyclopropyl-3-(3-(((6-(2-fluoro-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-5-neopentylpyridin-3-yl)oxy)methyl)phenyl)propanoate (84.1 mg) in ethanol (2.85 mL) was added 2N aqueous sodium hydroxide (357 μl) solution, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was cooled to 0° C., neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and 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 (52.8 mg) as a white amorphous solid.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried 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-445ddb13a3eb4ccc9d083a4509a3a42f
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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