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Hydrochloric Acid → [Rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid

HRID 394229
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 394229
C([O:3][C:4](=[O:34])[CH:5]([O:31][CH2:32][CH3:33])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=3)[S:18][CH:19]=2)=[C:9]([CH3:30])[CH:8]=1)C.[OH-].[Li+].Cl.S([O-])(O)(=O)=O.[K+]>CO>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:18][CH:19]=[C:15]([CH2:14][O:13][C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([O:31][CH2:32][CH3:33])[C:4]([OH:34])=[O:3])=[CH:8][C:9]=3[CH3:30])[N:16]=2)=[CH:25][CH:24]=1)([CH3:29])([CH3:28])[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 68616333[Rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester

Produkt 1

HCID 22647524[Rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid
Ausbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

140 mg of [rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester (0.29 mmol) were dissolved in 5 ml of methanol; 1 ml of a 2N aqueous lithium hydroxide solution was added and the reaction mixture was stirred at 55° C. for 1 h. After cooling to room temperature, 1 ml of a 2N aqueous hydrochloric acid solution and 0.5 ml of a saturated solution of potassium hydrogen sulfate were added. The reaction mixture was then extracted with two 10 ml portions of dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate and evaporated, leaving 130 mg (98.6% of theory) of [rac]-3-{4-[2-(4-tert-butyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-2-ethoxy-propionic acid as a colorless solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionThe reaction mixture was then extracted with two 10 ml portions of dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e816329aef26495b8872f233717c21e8
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06809110B2

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