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Sodium Methoxide → Sodium 1-(ethoxycarbonyl)-6-(4-fluorobenzyl)-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-4-olate

HRID 1817313
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1817313
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([OH:23])[CH:11]=[N+:12]([O-])[C:13]=3[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]2=[O:24])=[CH:4][CH:3]=1.C[O-:28].[Na+:29]>C(OC(=O)C)(=O)C>[CH2:20]([O:19][C:17]([C:13]1[NH:12][C:11](=[O:28])[C:10]([O-:23])=[C:9]2[C:14]=1[CH2:15][CH2:16][N:7]([CH2:6][C:5]1[CH:25]=[CH:26][C:2]([F:1])=[CH:3][CH:4]=1)[C:8]2=[O:24])=[O:18])[CH3:21].[Na+:29]
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Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 69064622Ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide

Produkt 1

HCID 69058491Sodium 1-(ethoxycarbonyl)-6-(4-fluorobenzyl)-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-4-olate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

To ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide (2.3 gm, 6.38 mmol) in neat acetic anhydride (24 mL) was stirred under nitrogen at 100° C. for 1 hour. The reaction was concentrated to an oil under reduced pressure and dry methanol (20 mL) was added followed by a methanolic sodium methoxide solution (30% by wt) (4.54 mL, 25.2 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to an oil under reduced pressure and crystallized from a small amount of methanol (˜5 mL). The crystals were collected by filtration, washed an additional 10 mL of methanol and dried in vacuo to give the desired product.

Aufarbeitung

  1. concentrationThe reaction was concentrated to an oil under reduced pressure and dry methanol (20 mL)
  2. additionwas added
  3. concentrationThe reaction was then concentrated to an oil under reduced pressure
  4. customcrystallized from a small amount of methanol (˜5 mL)
  5. filtrationThe crystals were collected by filtration
  6. washwashed an additional 10 mL of methanol
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9a04d33299314aafa77c5b30e0885013
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07598264B2

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