Phosphoric Acid → 4-tert-butoxy-2-(5-isoquinolinyl)-4-oxobutanoic Acid

HRID 586049

Reaktionsgleichung

Reaktionsgleichung von HRID 586049
[CH:1]1[C:10]2[C:5](=[C:6]([CH:11]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:12]([O:14]CC)=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[Li+].[OH-].OP(O)(O)=O>CO.O>[C:21]([O:20][C:18](=[O:19])[CH2:17][CH:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][N:2]=[CH:1]2)[C:12]([OH:14])=[O:13])([CH3:24])([CH3:22])[CH3:23]

Komponenten

5

Edukt 3

HCID 1004Phosphoric AcidHCID 3939Lithium HydroxideHCID 57494893HCID 57494893, Verbindung

Produkt 1

HCID 223375714-tert-butoxy-2-(5-isoquinolinyl)-4-oxobutanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

4-Tert-butyl 1-ethyl 2-(5-isoquinolinyl)succinate (1.00 g, 3.04 mmol) and LiOH (0.29 g) were stirred in MeOH:H2O (3:1, 20 mL) at room temperature for 5 hours. The solution was poured into aqueous H3PO4 (0.1M, 30 mL) and extracted with CHCl3:IPA (3:1, 30 mL×3). The extracts were combined, dried (MgSO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. MS (ESI+) m/z 302 (M+H)+; MS (ESI−) m/z 300 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.28 (s, 9H), 2.74 (dd, J1 16.7, J2 6.1, 1H), 3.10 (dd, J1 9.5, J2 6.1, 1H), 4.68 (dd, J1 16.7, J2 9.5, 1H), 7.70 (m, 2H), 8.05 (m, 2H), 8.57 (d, J 6.1, 1H), 9.33 (s, 1H); Anal. Calcd for C17H19NO4+1.25H2O: C, 63.05; H, 6.69. Found: C, 63.27; H, 6.95.

Aufarbeitung

  1. extractionextracted with CHCl3:IPA (3:1, 30 mL×3)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-715e1839ffe049ed9ed9799f9dc4647d
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933311B2

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