Hydrochloric Acid → 5-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-5-oxo-pentanoic Acid

HRID 11713

Reaktionsgleichung

Reaktionsgleichung von HRID 11713
C([O:3][C:4](=[O:37])[CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][CH2:18][C:19]([N:21]1[CH2:26][C@H:25]([CH3:27])[N:24]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:23][C@H:22]1[CH3:36])=[O:20])=[O:9])C.O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH2:18][C:19]([N:21]2[CH2:26][C@H:25]([CH3:27])[N:24]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[CH2:23][C@H:22]2[CH3:36])=[O:20])=[C:10]([C:8](=[O:9])[CH2:7][CH2:6][CH2:5][C:4]([OH:37])=[O:3])[CH:15]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 696556725-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-5-oxo-pentanoic Acid Ethyl Ester

Produkt 1

HCID 696556475-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-5-oxo-pentanoic AcidAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 5-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-5-oxo-pentanoic acid ethyl ester (0.089 g, 0.17 mmol) in 2:2:1 tetrahydrofuran:methanol:H2O (2 mL) was added lithium hydroxide hydrate (0.025 g, 0.60 mmol). The reaction was stirred at ambient temperature for 4 hours. The pH was then adjusted to 4 with 0.2 M hydrochloric acid. The solution was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Anion exchange chromatography (MCX) provided the title compound (0.014 g, LRMS: 505.5, 507.5).

Aufarbeitung

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-752ded381fa944ca81f476cb0dabaa2b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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