Methanol → (5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-acetic Acid

HRID 11721

Reaktionsgleichung

Reaktionsgleichung von HRID 11721
C([O:3][C:4](=[O:34])[CH2:5][NH:6][C:7]1[C:8]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)C.CO.O1CCCC1.O.[OH-].[Li+]>[Cl-].[Na+].O.O>[Cl:13][C:11]1[CH:12]=[C:7]([NH:6][CH2:5][C:4]([OH:34])=[O:3])[C:8]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[N:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69655410(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-acetic Acid Ethyl Ester

Produkt 1

HCID 69655388(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-acetic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-ylamino)-acetic acid ethyl ester (0.080, 0.16 mmol) in 2:2:1 methanol:tetrahydrofuran:water (1.5 mL) was added lithium hydroxide monohydrate (0.015 g, 0.36 mmol). The reaction was stirred at ambient temperature for 3 hours. The pH of the solution was adjusted to ˜4 by the addition of 0.2 M hydrochlroric acid, then diluted with brine and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The product was purified by anion exchange chromatography to give the title compound as its acetic acid addition salt (0.058 g, LRMS: 465.1, 467.2).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by anion exchange chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f53a8ebd21843f08b0582a455ef54ab
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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