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

HRID 19168
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 19168
C([O:3][C:4](=[O:27])[C@@H:5]([N:10]1[CH2:14][C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]3[CH2:24][CH2:23]3)[C:17]=2[F:25])=[CH:12][C:11]1=[O:26])[CH2:6][CH:7]([CH3:9])[CH3:8])C.O.[OH-].[Li+]>O1CCCC1>[CH:22]1([C:18]2[C:17]([F:25])=[C:16]([CH:21]=[CH:20][CH:19]=2)[O:15][C:13]2[CH2:14][N:10]([C@@H:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:27])=[O:3])[C:11](=[O:26])[CH:12]=2)[CH2:23][CH2:24]1
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Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 66895408(S)-2-[4-(3-cyclopropyl-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester

Produkt 1

HCID 66894750(S)-2-[4-(3-cyclopropyl-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acidAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution containing (S)-2-[4-(3-cyclopropyl-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester (0.800 g, 0.002 mol) in tetrahydrofuran (30 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 15 mL, 0.008 mol). The mixture was stirred at room temperature for 1 h, 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-(3-cyclopropyl-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid (0.71 g, 96%) as a yellow solid.

Aufarbeitung

  1. customthe solvents evaporated
  2. dissolutionThe residue was dissolved in water
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d267419f2f8c441f99fb58fbcbd1ba5f
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07741327B2

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