Citric Acid → HCID 16719112, Verbindung

HRID 751448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751448
C([O:3][C:4](=[O:34])[C:5]([CH3:33])([CH3:32])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:12][CH:13]=2)[CH:8]=1)C.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCOC(C)=O.O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:15]2[C:14]3[C:9](=[N:10][C:11]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)=[CH:12][CH:13]=3)[CH:8]=[C:7]2[CH2:6][C:5]([CH3:33])([CH3:32])[C:4]([OH:34])=[O:3])=[CH:18][CH:19]=1

Komponenten

8

Edukt 4

HCID 311Citric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 597547723-[1-(4-Chloro-benzyl)-5-(pyridin-2-ylmethoxy)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester

Produkt 1

HCID 16719112HCID 16719112, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-[1-(4-Chloro-benzyl)-5-(pyridin-2-ylmethoxy)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (0.024 g, 0.05 mmol) was dissolved in THF (0.1 mL), MeOH (0.1 mL), and H2O (0.1 mL). LiOH (0.008 g, 0.20 mmol) was added and the reaction was heated to 60° C. for 2 hours. Once no starting material was seen by LCMS, the reaction was cooled to room temperature and diluted with EtOAc and water. The mixture was neutralized with solid citric acid to ˜pH 5, the aqueous layer was extracted three times with EtOAc, the combined organics were washed twice with water, once with brine, dried over MgSO4, filtered and concentrated to give the desired acid. LCMS (ESI) M+H 450.

Aufarbeitung

  1. temperaturethe reaction was cooled to room temperature
  2. extractionthe aqueous layer was extracted three times with EtOAc
  3. washthe combined organics were washed twice with water, once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b1879299e6d94ae58214cbcd84748959
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405302B2

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