Hydrochloric Acid → HCID 25254148, compound

HRID 333776Notes

Reaction equation

HRID 333776 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([C:12]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH3:14])[CH:9]=[CH:8][N:7]=1.[OH-].[Na+].Cl>CO>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH:13]([CH3:14])[C:12]([C:10]1[CH:9]=[CH:8][N:7]=[C:6]([O:5][CH2:4][C:3]([OH:28])=[O:2])[CH:11]=1)([OH:27])[C:23]([F:25])([F:26])[F:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25254606{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl ester

Product 1

HCID 25254148HCID 25254148, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

To a solution of {4-[2-(2,4-dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl ester (127 mg) in methanol (2 mL) was added an aqueous solution of NaOH (1N, 0.58 mL) and the mixture was allowed to stir at 55° C. for 2 hours. The pH of the mixture was adjusted to pH 2 with aqueous 1N HCl solution and methanol was removed by evaporation. The aqueous solution was extracted twice with ethyl acetate and the organic layers were washed with brine, dried and evaporated. The residual oil was stirred in hexane (5 mL) over night and the suspension was filtered to give the title compound as a colorless powder (96 mg). MS (m/e): 424.2 (MH)+.

Workup

  1. customwas removed by evaporation
  2. extractionThe aqueous solution was extracted twice with ethyl acetate
  3. washthe organic layers were washed with brine
  4. customdried
  5. customevaporated
  6. stirringThe residual oil was stirred in hexane (5 mL) over night
  7. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-a50d9b3f1a80443ca6ceeaec97cd1a31
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

Loading…