Methyl acetoacetate → methyl-(E)-7[5-(4-fluorophenyl)1,2-dihydro-7-isopropyl-2-oxo-1,8-naphthyridin-6-yl]-5-hydroxy-3-oxo-hept-6-enoate

HRID 1087049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087049
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:32](/[CH:33]=[CH:34]/[CH:35]=[O:36])=[C:31]([CH:37]([CH3:39])[CH3:38])[N:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][C:27](=[O:40])[NH:28]3)=[CH:19][CH:18]=1>O1CCCC1.CCCCCC.O.C(O)(=O)C>[CH3:8][O:7][C:1](=[O:6])[CH2:2][C:3](=[O:4])[CH2:5][CH:35]([OH:36])/[CH:34]=[CH:33]/[C:32]1[C:23]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[C:24]2[C:29](=[N:30][C:31]=1[CH:37]([CH3:39])[CH3:38])[NH:28][C:27](=[O:40])[CH:26]=[CH:25]2

Komponenten

9

Edukt 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 14850559(E)-3-[5-(4-Fluorophenyl)-1,2-dihydro-7-isopropyl-2-oxo1, 8-naphthyridin-6-yl]-prop-2-enalHCID 178418339Butyllithium

Produkt 1

HCID 14850560methyl-(E)-7[5-(4-fluorophenyl)1,2-dihydro-7-isopropyl-2-oxo-1,8-naphthyridin-6-yl]-5-hydroxy-3-oxo-hept-6-enoateAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

5.47 g (50.7 mmol) of methyl acetoacetate in 5 ml of tetrahydrofuran are added dropwise at -5° C. to 0° C. under argon to a suspension of 1.69 g (56.4 mmol) of 80% strength sodium hydride in 50 ml of anhydrous tetrahydrofuran. After 15 min, 41 ml (67.6 mmol) of 15% strength butyl lithium in hexane are added dropwise at the same temperature and, after a further 15 min, a solution of 5.68 g (16.9 mmol) of the compound from Example 5 in 150 ml of tetrahydrofuran. The mixture is stirred at room temperature for one hour, then 11.2 g of acetic acid in 120 ml of water are cautiously added dropwise and the mixture is extracted three times with ethyl acetate. The organic phases are washed with saturated sodium hydrogen carbonate and sodium chloride solution, dried over sodium sulphate and concentrated. 7.8 g of crude methyl-(E)-7[5-(4 -fluorophenyl)1,2-dihydro-7-isopropyl-2-oxo-1,8-naphthyridin-6-yl]-5-hydroxy-3-oxo-hept-6-enoate are obtained as orange oil.

Aufarbeitung

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe organic phases are washed with saturated sodium hydrogen carbonate and sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cd2091a2d3424ebba3eb6919e694075e
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034399

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