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

HRID 1951605
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1951605
[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]
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Komponenten

6

Edukt 3

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

Produkt 1

HCID 690000763-[4-[3-[4-Hexyl-2-(4-methylphenyl)thiazol-5-yl]propionyl]-2-methylphenyl]propionic acidAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c61ac0d13f0b438db192618ee1d2bc24
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08404726B2

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