Hydrochloric Acid → HCID 25254451, compound

HRID 333803Notes

Reaction equation

HRID 333803 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-b20f0e2a29154dfc952f007c2e347b4f
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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