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Hydrochloric Acid → 2-{3-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acid

HRID 502390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 502390
C([O:3][C:4](=[O:38])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:37])[NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[C:27]([F:33])=[C:26]([O:34][CH2:35][CH3:36])[CH:25]=3)[CH2:19][CH2:18]2)[CH:10]=1)([CH3:7])[CH3:6])C.[Li+].[OH-].O.Cl>C1COCC1.CO>[CH2:31]([O:30][C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([O:34][CH2:35][CH3:36])[C:27]=1[F:33])[CH2:23][N:20]1[CH2:19][CH2:18][CH:17]([NH:16][C:15]([C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:38])=[O:3])=[O:37])[CH2:22][CH2:21]1)[CH3:32]
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 684554712-{3-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acid ethyl ester

Produkt 1

HCID 684590972-{3-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acidAusbeute 26,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815
MeOH tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

0.54 g (1.0 mmol) of 2-{3-[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-phenoxy}-2-methyl-propionic acid ethyl ester (example 50k) was reacted with 1.0 mL of LiOH/water (1.0 molar) in 15 mL of THF/MeOH (2:1) at 0° C. and subsequent temperature increase to rt. After 5 h, the reaction mixture was poured into crashed ice, the pH was adjusted to ˜7.0 with aq. HCl (1N) and the reaction mixture was extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. The crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH) to yield 0.135 g of the title compound as colorless solid. MS: 503.1 (MH+).

Aufarbeitung

  1. additionthe reaction mixture was poured
  2. extractionthe reaction mixture was extracted twice with MeCl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated i.V
  7. customThe crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-eca27cca77a246f891910ada7d26a9b7
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772253B2

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