Lithium hydroxide, monohydrate → (S)-2-{4-[2-fluoro-3-(1-hydroxy-1-methyl-ethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid

HRID 19162

Reaktionsgleichung

C[O:2][C:3](=[O:27])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:24])([CH3:23])[CH3:22])[C:16]=2[F:25])=[CH:11][C:10]1=[O:26])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1>[F:25][C:16]1[C:17]([C:21]([OH:24])([CH3:22])[CH3:23])=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][C:12]1[CH2:13][N:9]([C@@H:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:27])=[O:2])[C:10](=[O:26])[CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution containing (S)-2-{4-[2-fluoro-3-(1-hydroxy-1-methyl-ethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid methyl ester (2.00 g, 0.005 mol) in tetrahydrofuran (20 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 20 mL, 0.010 mol). The mixture was stirred at 25° C. for 2H, and the solvents evaporated. The residue was dissolved in water and washed with diethyl ether, and the diethyl ether layer discarded. The aqueous phase was acidified with dilute hydrochloric acid (pH <2), and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford (S)-2-{4-[2-fluoro-3-(1-hydroxy-1-methyl-ethyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid (1.93 g, 100%) as a fluffy solid.

Aufarbeitung

customthe solvents evaporated
dissolutionThe residue was dissolved in water
washwashed with diethyl ether
extractionextracted with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-3f07ae2b87504477a8b951d44def6dfc
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07741327B2

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