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Methanol → methyl 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoate

HRID 910296
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 910296
[CH2:1]([O:3][C@@H:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:19][C:18]([NH:20][CH3:21])=[N:17][CH:16]=2)=[CH:11][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:2].[OH-].[Na+].[CH3:24]O>S(=O)(=O)(O)O.O>[CH2:1]([O:3][C@@H:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[S:19][C:18]([NH:20][CH3:21])=[N:17][CH:16]=2)=[CH:13][CH:14]=1)[C:5]([O:7][CH3:24])=[O:6])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 866062382(S)-Ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoic acid

Produkt 1

HCID 86606239methyl 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

0.5 g (1.6 mmol) of 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoic acid in 10 ml of methanol and a few drops of sulfuric acid is heated at 60° C. for 2 hours. The reaction medium is cooled, diluted with water, neutralized to pH 7 with aqueous 1M sodium hydroxide solution and then extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 50/50 heptane/ethyl acetate mixture. 0.34 g (67%) of methyl 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoate is obtained in the form of a yellow solid.

Aufarbeitung

  1. temperatureThe reaction medium is cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 50/50 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-510f03c5144c42e1898a4addf4573f3e
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08022079B2

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