Citric Acid → (R)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid

HRID 2175175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175175
C([O:3][C:4](=[O:36])[CH2:5][C@@H:6]([N:13]1[C:21]2[CH:20]=[C:19]([CH3:22])[N:18]=[CH:17][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+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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[CH:17]=[N:18][C:19]([CH3:22])=[CH:20][C: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

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 58497394(R)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester

Produkt 1

HCID 58497450(R)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-3-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester (80 mg, 0.17 mmol) in MeOH (5 mL) was added 2N NaOH (2 mL). The reaction mixture was stirred at room temperature for 2 hours. The reaction was then treated with 0.5N citric acid solution. The reaction mixture was extracted with CH2Cl2 twice. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 10:5 CH2Cl2:MeOH as an eluent to afford 67 mg (89%) of the title compound as a white floppy solid. LCMS, M++1, m/z: 456.15.

Aufarbeitung

  1. extractionThe reaction mixture was extracted with CH2Cl2 twice
  2. dry with materialThe 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-a1ec4ed75c0447e79629ac05ba981a88
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062056B2

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