Hydrochloric Acid → (S)-3-cyclohexyl-2-(4-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid

HRID 2365734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365734
C[O:2][C:3](=[O:23])[C@@H:4]([N:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[F:21])[C:13]1=[O:22])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH:6]1([CH2:5][C@H:4]([N:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[F:21])[C:13]2=[O:22])[C:3]([OH:23])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70945620(S)-3-cyclohexyl-2-(4-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester

Produkt 1

HCID 67484493(S)-3-cyclohexyl-2-(4-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of (S)-3-cyclohexyl-2-(4-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (311 mg, 0.97 mmol) in tetrahydrofuran (6 mL) at room temperature was treated with a mixture of lithium hydroxide monohydrate (82 mg, 1.95 mL) in water (6 mL). The reaction mixture was then stirred at room temperature until the reaction was complete by TLC (˜2 h). After this time, the reaction mixture was treated with 1N aqueous hydrochloric acid solution until the pH=2. The reaction mixture was then extracted with ethyl acetate (3×20 mL). The combined organic layers were then dried over magnesium sulfate, filtered to remove the drying agent and the filtrate was concentrated in vacuo to afford (S)-3-cyclohexyl-2-(4-fluoro-1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (230 mg, 78%) as a white solid.

Aufarbeitung

  1. customwas complete by TLC (˜2 h)
  2. extractionThe reaction mixture was then extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers were then dried over magnesium sulfate
  4. filtrationfiltered
  5. customto remove the drying agent
  6. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e887b22554a54651b9d19a216ae33321
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697705B2

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