Water → HCID 86718270, compound

HRID 625665Notes

Reaction equation

HRID 625665 reaction equation
O=C1[N:6]([C:7]2[CH:18]=[CH:17][C:10]([CH2:11][NH:12][C:13](=[O:16])[CH2:14][CH3:15])=[C:9]([C:19]([F:22])([F:21])[F:20])[CH:8]=2)[CH2:5][C:4]([C:27]2[CH:32]=[C:31]([Cl:33])[C:30]([Cl:34])=[C:29]([Cl:35])[CH:28]=2)([C:23]([F:26])([F:25])[F:24])[O:3]1.O.[OH-].[K+]>O1CCOCC1>[F:25][C:23]([F:24])([F:26])[C:4]([OH:3])([C:27]1[CH:28]=[C:29]([Cl:35])[C:30]([Cl:34])=[C:31]([Cl:33])[CH:32]=1)[CH2:5][NH:6][C:7]1[CH:18]=[CH:17][C:10]([CH2:11][NH:12][C:13](=[O:16])[CH2:14][CH3:15])=[C:9]([C:19]([F:20])([F:21])[F:22])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86718271HCID 86718271, compound

Product 1

HCID 86718270HCID 86718270, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
70 °C

Procedure

N-{4-[2-oxo-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-1,3-oxazolidin-3-yl]-2-(trifluoro-methyl)benzyl}propane amide (542 mg) was added to a solution of 1,4-dioxane (10 mL), water (10 mL) and potassium hydroxide (108 mg), and stirred at 70° C. for 1 hour. After the reaction, 1,4-dioxane was distilled off under reduced pressure, and conc. hydrochloric acid (70 mg) was added and stirred under ice cooling. The resultant was extracted with ethyl acetate, washed with water and saturated brine, and the organic layer is dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residues were purified by silica-gel column chromatography to give N-[4-{[3,3,3-trifluoro-2-hydroxy-2-(3,4,5-trichlorophenyl)propyl]amino}-2-(trifluoromethyl)benzyl]propane amide (503 mg).

Workup

  1. distillationwas distilled off under reduced pressure, and conc. hydrochloric acid (70 mg)
  2. additionwas added
  3. stirringstirred under ice cooling
  4. extractionThe resultant was extracted with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residues were purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-b04442bae3b34b6881834cbf2493850e
Source dataset
uspto-grants-2016_04
Patent number
US09307764B2

Reaction notes

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