Hydrochloric Acid → 6-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxymethyl)-nicotinic acid

HRID 11711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11711
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH2:20][C:21]([N:23]2[CH2:28][C@H:27]([CH3:29])[N:26]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH2:25][C@H:24]2[CH3:38])=[O:22])=[N:6][CH:5]=1.O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[Cl:18][C:16]1[CH:15]=[CH:14][C:13]([O:19][CH2:20][C:21]([N:23]2[CH2:28][C@H:27]([CH3:29])[N:26]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[CH2:25][C@H:24]2[CH3:38])=[O:22])=[C:12]([CH:17]=1)[O:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:39])=[O:2])=[CH:5][N:6]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 696553196-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxymethyl)-nicotinic Acid Methyl Ester

Produkt 1

HCID 696555716-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxymethyl)-nicotinic acidAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenoxymethyl)-nicotinic acid methyl ester (0.13 g, 0.23 mmol) in 2:2:1 tetrahydrofuran:methanol:H2O (2 mL) was added lithium hydroxide hydrate (0.020 g, 0.48 mmol). The reaction was stirred at ambient temperature for 3 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. Trituration in diethyl ether provided the title compound (0.034 g, LRMS: 542.4, 544.5).

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-f2ea5543ec26465da37eff30af9f6664
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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