Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate → 3-[(Dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoic Acid

HRID 14305

Reaktionsgleichung

Reaktionsgleichung von HRID 14305
[CH2:1]([N:4]([CH2:22][CH2:23][CH3:24])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:6])[CH2:2][CH3:3]>O1CCCC1.CO.O.O.[OH-].[Li+]>[CH2:22]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:6])[CH2:23][CH3:24]

Komponenten

4

Edukt 1

HCID 21086169Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate

Produkt 1

HCID 210857833-[(Dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 168937Lithium hydroxide, monohydrateLösungsmittelHCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

Methyl 3-[(dipropylamino)carbonyl]-5-(1,3-thiazol-2-yl)benzoate (4.4 g, 12.8 mmol) is dissolved in 1:1:1 tetrahydrofuran/methanol/water (60 mL), and lithium hydroxide monohydrate is added (1.1 g, 25.6 mmol), and the reaction stirred 15 min. The solution is concentrated under reduced pressure and diluted in chloroform. The solution is washed with water and saturated sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to give the title compound. ESI MS m/z 333.1 [M+H]+.

Aufarbeitung

  1. additionis added (1.1 g, 25.6 mmol)
  2. concentrationThe solution is concentrated under reduced pressure
  3. additiondiluted in chloroform
  4. washThe solution is washed with water and saturated sodium bicarbonate
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4fb70e28143a441893afb610343e3a5c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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