Sodium Methoxide → Sodium 1-(ethoxycarbonyl)-6-(4-fluorobenzyl)-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-4-olate
Reaction equation
[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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- concentrationThe reaction was concentrated to an oil under reduced pressure and dry methanol (20 mL)
- additionwas added
- concentrationThe reaction was then concentrated to an oil under reduced pressure
- customcrystallized from a small amount of methanol (˜5 mL)
- filtrationThe crystals were collected by filtration
- washwashed an additional 10 mL of methanol
- customdried in vacuo
Sources & evidence
- ORD record
- ord-9a04d33299314aafa77c5b30e0885013
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598264B2
Reaction notes
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