Methanol → 2-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoic acid

HRID 2424975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2424975
[OH-].[Li+].[CH2:3]([C:5]1[N:6]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH:30]([CH3:35])[C:31]([O:33]C)=[O:32])[CH:25]=[CH:24]4)=[N:14][CH:15]=2)[S:8][CH:9]=1)[CH3:4].CO.O>C1COCC1>[CH2:3]([C:5]1[N:6]=[C:7]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH:30]([CH3:35])[C:31]([OH:33])=[O:32])[CH:25]=[CH:24]4)=[N:14][CH:15]=2)[S:8][CH:9]=1)[CH3:4]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 57845392methyl 2-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoate

Produkt 1

HCID 115397032-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoic acidAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide (0.05 g, 2.15 mmol) was added to a solution of methyl 2-[5-(3-{[5-(4-ethyl-1,3-thiazol-2-yl)-2-pyridinyl]oxy}propoxy)-1H-indol-1-yl]propanoate (Example 69, 0.1 g, 0.21 mmol) in a mixture of THF (2 mL), methanol (2 mL), and water (1 mL). The reaction mixture was stirred at rt for 18 h and then concentrated under reduced pressure. The residue was diluted with water and acidified with 5% H3PO4. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to give the title compound as a solid (0.079 g, 82%). 1H NMR (400 MHz, CD2Cl2) δ 8.45 (dd, 1H), 7.94 (dd, 1H), 7.08-6.62 (m, 6H), 6.22 (d, 1H), 4.94 (qt, 1H), 4.37 (t, 2H), 4.00 (t, 2H), 2.66 (qt, 2H), 2.31-2.07 (m, 2H), 1.60 (d, 3H), 1.15 (t, 3H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dcfa237f98834a3ea9e5130d4176b7ff
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964622B2

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