Hydrochloric Acid → HCID 9822765, compound

HRID 1826077Notes

Reaction equation

HRID 1826077 reaction equation
[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH2:18][C:19](=[O:31])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:11]=1)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[Na+].Cl>C(O)C>[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH2:18][C:19](=[O:31])[NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=2)[CH:11]=1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10863050HCID 10863050, compound

Product 1

HCID 9822765HCID 9822765, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-ethyl-3-[4-methoxy-3-[[N-[4-(trifluoromethyl)phenyl]carbamoyl]methyl]phenyl]propanoate (206 mg, 0.471 mmol), ethanol (5 mL) and 10% aqueous solution of sodium hydroxide (3 mL) were mixed and the mixture was stirred for 6 hours at room temperature. The reaction mixture was poured into ice water and made acidic with 1 mol/L hydrochloric acid, which was then extracted with ethyl acetate. The extracte was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=4:1→1:1 v/v) and recrystallized from a mixed solvent of n-hexane with ethyl acetate to afford 142 mg (73%) of the title compound as colorless powder.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extracte was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=4:1→1:1 v/v)
  6. customrecrystallized from a mixed solvent of n-hexane with ethyl acetate

Sources & evidence

ORD record
ord-c7d8976755c546ea8e8c7c32d6598b99
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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