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

HRID 1627188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627188
[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-eb2988e9614843a4b895f8a19a87d97d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785429B2

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