Methanol → (R)-3-Methyl-2-(3-oxopyrrolo [4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)butanoic acid

HRID 1968284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968284
[CH3:1][CH:2]([CH3:34])[C@@H:3]([N:11]1[C:20](=[O:21])[C:19]2=[CH:22][N:23](S(C3C=CC(C)=CC=3)(=O)=O)[C:17]3[C:18]2=[C:13]([CH:14]=[CH:15][N:16]=3)[CH2:12]1)[C:4]([O:6]C(C)(C)C)=[O:5].CO.[OH-].[Na+]>C(Cl)Cl>[CH3:1][CH:2]([CH3:34])[C@@H:3]([N:11]1[C:20](=[O:21])[C:19]2=[CH:22][NH:23][C:17]3[C:18]2=[C:13]([CH:14]=[CH:15][N:16]=3)[CH2:12]1)[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67224983(R)-tert-Butyl 3-methyl-2-(3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)butanoate

Produkt 1

HCID 67224069(R)-3-Methyl-2-(3-oxopyrrolo [4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)butanoic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (R)-tert-Butyl 3-methyl-2-(3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)butanoate (840 mg, 1.74 mmol), MeOH (4 mL), and aqueous NaOH (1N, 2 mL) was stirred for 40 min at room temperature. The material was diluted with DCM and washed with brine. The organics were dried over MgSO4 and concentrated in vacuo. Purification by silica gel chromatography (5% MeOH/DCM) gave a yellow oil (390 mg), which dissolved in TFA/DCM (50%) and stirred at room temperature for 1 h. The solution was concentrated and dried under vacuum to give the title compound as a tan solid (320 mg, 67%). 1H NMR (500 MHz, CD3OD) δ 0.88 (d, J=7.0 Hz, 3H), 1.10 (d, J=7.0 Hz, 3H), 2.35-2.44 (m, 1H), 4.95-5.33 (m, 3H), 7.34 (d, J=6.0 Hz, 1H), 7.90 (s, 1H), 8.33 (d, J=6.0 Hz, 1H). [M+H] calc'd for C14H15N3O3, 274; found, 274.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography (5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a4b612d856f4494d97ff242801f428d6
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420816B2

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