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Hydrochloric Acid → (R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid

HRID 2175170
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2175170
C([O:3][C:4](=[O:36])[CH2:5][C@@H:6]([N:13]1[C:17]2=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=[C:16]2[N:15]([CH2:23][C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[CH3:33])[N:26]([CH3:34])[CH:25]=2)[C:14]1=[O:35])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>CO>[CH3:34][N:26]1[C:27]2[C:32](=[C:31]([CH3:33])[CH:30]=[CH:29][CH:28]=2)[C:24]([CH2:23][N:15]2[C:16]3[C:17](=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[N:13]([C@@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:5][C:4]([OH:36])=[O:3])[C:14]2=[O:35])=[CH:25]1
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58497460(R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester

Produkt 1

HCID 58497404(R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acidAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-3-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester (200 mg, 0.41 mmol) in MeOH (5 mL) was added 2N NaOH (2 mL). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then treated with 1N HCl and extracted with CH2Cl2 twice. The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 144 mg (76%) of the title compound as off-white solid. LCMS, M++1, m/z: 455.00.

Aufarbeitung

  1. extractionextracted with CH2Cl2 twice
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-9ba96d6b36d54a8b93b867cf9a3ebf10
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09062056B2

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