Hydrochloric Acid → 3-[4-[3-[4-Hexyl-2-(4-methylphenyl)thiazol-5-yl]propionyl]-2-methylphenyl]propionic acid

HRID 1951605Notes

Reaction equation

HRID 1951605 reaction equation
[CH2:1]([C:7]1[N:8]=[C:9]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[S:10][C:11]=1[CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])=[C:18]([CH3:28])[CH:17]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.[OH-].[Li+].Cl>C(O)C.O>[CH2:1]([C:7]1[N:8]=[C:9]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[S:10][C:11]=1[CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:18]([CH3:28])[CH:17]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 16755796Methyl 3-[4-[3-[4-hexyl-2-(4-methylphenyl)thiazol-5-yl]propionyl]-2-methylphenyl]propionate

Product 1

HCID 690000763-[4-[3-[4-Hexyl-2-(4-methylphenyl)thiazol-5-yl]propionyl]-2-methylphenyl]propionic acidYield 86.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

The obtained methyl 3-[4-[3-[4-hexyl-2-(4-methylphenyl)thiazol-5-yl]propionyl]-2-methylphenyl]propionate (45 mg, 0.0915 mmol) was suspended in ethanol (2 mL) and water (1 mL). Lithium hydroxide monohydrate (12 mg, 0.275 mmol) was added to the suspension. The mixture was refluxed for 1 hour. 1N hydrochloric acid (5 mL) and ice-cooled water (2 mL) were added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure. The obtained residue was recrystallized with hexane and ethyl acetate to give the desired compound (38 mg) as while crystalline product (yield 87%).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. additionwere added to the mixture
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe obtained residue was recrystallized with hexane and ethyl acetate

Sources & evidence

ORD record
ord-c61ac0d13f0b438db192618ee1d2bc24
Source dataset
uspto-grants-2013_03
Patent number
US08404726B2

Reaction notes

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