Lithium Hydroxide → (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid
Reaktionsgleichung
C([O:3][C:4](=[O:25])[C@H:5]([N:11]1[CH2:15][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:13][C:12]1=[O:24])[CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])C.[OH-].[Li+]>O1CCCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:14]1[CH2:15][N:11]([C@H:5]([CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])[C:4]([OH:25])=[O:3])[C:12](=[O:24])[CH:13]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 5 °C
Versuchsvorschrift
A solution of (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester (1.25 g, 3.42 mmol) in tetrahydrofuran (14 mL) was treated with a 0.5N lithium hydroxide solution (4 mL) and stirred at 5° C. for 2 h. The mixture was concentrated in vacuo and the residue was dissolved in water (40 mL) and washed with diethyl ether. The organic phase was discarded and the aqueous layer acidified with 1N aqueous hydrochloric acid (10 mL) and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated in vacuo which afforded (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid (1.13 g, 98%) as a pale brown solid.
Aufarbeitung
- concentrationThe mixture was concentrated in vacuo
- dissolutionthe residue was dissolved in water (40 mL)
- washwashed with diethyl ether
- extractionextracted with ethyl acetate
- concentrationThe combined ethyl acetate layers were concentrated in vacuo which
Quellen und Nachweise
- ORD-Eintrag
- ord-22b8b902fbc346e48fdc89b7741c4918
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07741327B2
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