Lithium hydroxide, monohydrate → 3-[(Dipropylamino)carbonyl]-5-Ethylbenzoic Acid

HRID 14003

Reaktionsgleichung

Reaktionsgleichung von HRID 14003
O.[OH-].[Li+].[CH2:4]([N:7]([CH2:22][CH2:23][CH3:24])[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH2:20][CH3:21])[CH:19]=1)[C:13]([O:15]C)=[O:14])=[O:9])[CH2:5][CH3:6]>C1COCC1.CO.O.O.Cl>[CH2:22]([N:7]([CH2:4][CH2:5][CH3:6])[C:8]([C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH2:20][CH3:21])[CH:19]=1)[C:13]([OH:15])=[O:14])=[O:9])[CH2:23][CH3:24]

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 22593628Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

Produkt 1

HCID 225936423-[(Dipropylamino)carbonyl]-5-Ethylbenzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

Lithium hydroxide monohydrate (0.0680 g, 1.6 mmol) is added to a mixture of methyl 3-[(dipropylamino)carbonyl]-5-ethylbenzoate (PREPARATION 20, 0.450 g, 1.6 mmol) in a mixture of THF/methanol/water (2/1/1, 8 mL). The mixture is stirred at 20-25 degrees C. for 3 hours. The mixture is then diluted with water (20 mL) and hydrochloric acid (1 N) is added to bring the pH to less than 3. The aqueous mixture is extracted with ethyl acetate. The organic phase is separated and washed with saline, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound, MS (ESI+) for C16H23NO3 m/z (M+H)+=278.2.

Aufarbeitung

  1. additionis added
  2. extractionThe aqueous mixture is extracted with ethyl acetate
  3. customThe organic phase is separated
  4. washwashed with saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a595837486be4e039d4224f92ba8f393
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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