Hydrochloric Acid → HCID 25254451, compound

HRID 1097904Notes

Reaction equation

HRID 1097904 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:27])[C:14]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[CH:21]=2)([OH:19])[C:15]([F:18])([F:17])[F:16])=[C:9]([Cl:28])[CH:8]=1)C.[OH-].[Na+].O.Cl>C1COCC1>[Cl:28][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:29])=[O:3])[CH:12]=[CH:11][C:10]=1[CH:13]([CH3:27])[C:14]([C:20]1[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[CH:21]=1)([OH:19])[C:15]([F:16])([F:18])[F:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86629103HCID 86629103, compound

Product 1

HCID 25254451HCID 25254451, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenyl}-propionic acid ethyl ester (118 mg) was dissolved in THF (1 mL). To the solution was added 1M aq. NaOH (1 mL) to give a cloudy, light yellow mixture. The reaction was allowed to stir at RT for 2.5 hours; a clear solution was obtained at that time. Water was added and the pH was adjusted to pH=3 with dilute aqueous HCl. A colorless precipitate was formed. The mixture was extracted with ethyl acetate and the organic extracts were washed with brine, dried over Na2SO4 and evaporated. The title compound was obtained as a colorless solid (78 mg). MS (neg. ion, m/e)=420.1 (M−H)−.

Workup

  1. customto give a cloudy, light yellow mixture
  2. customa clear solution was obtained at that time
  3. customA colorless precipitate was formed
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-95f59796510e4ec4bffdd7b3f0b1bef6
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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